Heterocyclic hydrazide compound and pesticidal use of the same

ABSTRACT

A hydrazide compound represented by the formula (I), an N-oxide thereof or suitable salt thereof: has excellent pesticidal activity.

CONTINUING DATA

This application is a 371 of PCT/JP2008/057560 filed Apr. 11, 2008.

TECHNICAL FIELD

The present invention relates to a hydrazide compound and pesticidal useof the same.

BACKGROUND ART

WO 2002/070483 discloses several 5- and 6-membered heteroaromaticdiamide compounds activity. Furthermore, in WO 2007/020050 isheterobicylic diamide compounds described and their use of forcontrolling harmful pests in agriculture.

DISCLOSURE OF THE INVENTION

The present invention is intended to provide a compound having excellentefficacy of controlling pests.

The present inventors have intensively studied in order to find out acompound having excellent efficacy of controlling pests and, as aresult, found out that a hydrazide compound represented by the followingformula (1) has excellent controlling efficacy. Thus, the presentinvention has been completed.

According to the present invention, there is provided:

A hydrazide compound represented by the formula (1) (hereinafterreferred to as the present compound), an N-oxide thereof or suitablesalt thereof:

wherein

A¹ and A² independently represent an oxygen atom or a sulfur atom;

E represents, together with the two contiguous linking carbon atoms, a5- or 6-membered heteroaromatic ring system or a 8-, 9- or 10-memberedfused heterobicyclic ring system;

R¹ represents a hydrogen atom, C1-C6 alkyl optionally substituted withone or more halogen atoms, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6alkenyl optionally substituted with one or more halogen atoms, C2-C6alkynyl optionally substituted with one or more halogen atoms, C3-C6cycloalkyl optionally substituted with one or more halogen atoms, C1-C6alkylthio optionally substituted with one or more halogen atoms, C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms,C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6trialkylsilyl;

or represents phenyl, C7-C9 phenylalkyl or phenylcarbonyl: each saidphenyl ring optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl;

R² and R³ independently represent a hydrogen atom, C1-C6 alkyloptionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl,C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionally substituted with one ormore halogen atoms, C2-C6 alkenyl optionally substituted with one ormore halogen atoms, C2-C6 alkynyl optionally substituted with one ormore halogen atoms, C3-C6 cycloalkyl optionally substituted with one ormore halogen atoms, C1-C6 alkylthio optionally substituted with one ormore halogen atoms, C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms, C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C4-C6cycloalkylaminocarbonyl, or C3-C6 trialkylsilyl;

or represents phenyl, C7-C9 phenylalkyl or phenylcarbonyl: each saidphenyl ring optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl; or

R² and R³ are taken together with the two nitrogen atoms to which theyare attached to form a 5- to 8-membered ring containing two nitrogenatoms, one or more CH₂ or C(═O), and optionally one or two ring membersselected from the group consisting of (1) an oxygen atom, (2) a sulfuratom, (3) S(═O), (4) S(═O)₂ and (4) NR^(a) (wherein R^(a) representsC1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6alkoxycarbonyl optionally substituted with one or more halogen atoms, ora phenyl optionally substituted with one or more independentsubstituents from the group consisting of (1) a halogen atom, (2) cyano,(3) nitro, (4) C1-C6 alkyl optionally substituted with one or morehalogen atoms, (5) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (6) C1-C6 alkylthio optionally substituted with one ormore halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted withone or more halogen atoms, (8) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (9) C1-C6 alkylaminooptionally substituted with one or more halogen atoms, (10) C2-C6dialkylamino optionally substituted with one or more halogen atoms, (11)C2-C6 alkylcarbonyl optionally substituted with one or more halogenatoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms);

and wherein the ring at the carbon atoms is optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, (2) C1-C6 alkyl optionally substituted with oneor more halogen atoms, and (3) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms;

R⁴ represents a halogen atom, cyano, nitro, hydroxyl, carboxyl, C1-C6alkyl optionally substituted with one or more halogen atoms, C1-C6alkoxy optionally substituted with one or more halogen atoms, C2-C6cyanoalkyl, C2-C6 alkoxyalkyl optionally substituted with one or morehalogen atoms, C2-C6 alkenyl optionally substituted with one or morehalogen atoms, C2-C6 alkynyl optionally substituted with one or morehalogen atoms, C3-C6 cycloalkyl optionally substituted with one or morehalogen atoms, C1-C6 alkylthio optionally substituted with one or morehalogen atoms, C1-C6 alkylsulfinyl optionally substituted with one ormore halogen atoms, C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6cycloalkylamino, C2-C6 alkylcarbonyl optionally substituted with one ormore halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl,C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl;

or represents a phenyl, benzyl, phenoxy, or a 5- or 6-memberedheteroaromatic ring, each ring optionally substituted with one or moresubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl;

n represents an integer of 0 to 3 (provided that, when n is an integerof 2 or more, R⁴'s may be the same or different);

Q represents Q1, Q2, Q3, Q4, Q5 or Q6:

A³¹, A³², A³³ and A³⁴ represent an oxygen atom, or a sulfur atom;

m represents an integer of 0 to 2;

R⁶ represents a hydrogen atom; C2-C6 alkenyl optionally substituted withone or more halogen atoms; C2-C6 alkynyl optionally substituted with oneor more halogen atoms; C1-C6 alkyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (3) C1-C6 alkylthio optionally substituted with one ormore halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted withone or more halogen atoms, (5) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (6) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, and (7) C3-C6cycloalkyl optionally substituted with one or more halogen atoms; C3-C6cycloalkyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,and (2) C1-C6 alkyl optionally substituted with one or more halogenatoms; phenyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms, (5) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (6) C1-C6 alkylthio optionally substituted with oneor more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substitutedwith one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (9) C1-C6 alkylaminooptionally substituted with one or more halogen atoms, (10) C2-C6dialkylamino optionally substituted with one or more halogen atoms, (11)C2-C6 alkylcarbonyl optionally substituted with one or more halogenatoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; naphthyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms; 5-to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 3- to 8-memberednon-aromatic heterocyclic ring optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each saidphenyl ring optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms;

R⁷ and R⁸ represent C1-C6 alkyl optionally substituted with one or morehalogen atoms; C2-C6 alkoxyalkyl optionally substituted with one or morehalogen atoms; C2-C6 alkenyl optionally substituted with one or morehalogen atoms; C2-C6 alkynyl optionally substituted with one or morehalogen atoms; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms and (5) C1-C6alkoxy optionally substituted with one or more halogen atoms; or C7-C9phenylalkyl whose phenyl ring moiety optionally is substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

R⁹ and R¹⁰ independently represent a hydrogen atom; C1-C6 alkyloptionally substituted with one or more halogen atoms; C2-C6 alkoxyalkyloptionally substituted with one or more halogen atoms; C2-C6 alkenyloptionally substituted with one or more halogen atoms; C2-C6 alkynyloptionally substituted with one or more halogen atoms; C3-C6 cycloalkyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, and (2) C1-C6alkyl optionally substituted with one or more halogen atoms; phenyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; 5- to 6-membered heteroaryloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms and (5) C1-C6 alkoxy optionally substituted with one or morehalogen atoms; or C7-C9 phenylalkyl whose phenyl ring moiety optionallyis substituted with one or more independent substituents selected fromthe group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4)C1-C6 alkyl optionally substituted with one or more halogen atoms and(5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;R¹¹ represents C1-C6 alkyl optionally substituted with one or morehalogen atoms; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; or a phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 5- to 6-memberedheteroaryl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms; or 3- to 8-membered non-aromatic heterocyclicring optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, and (2) C1-C6alkyl optionally substituted with one or more halogen atoms;

R¹² and R¹³ independently represent C1-C6 alkyl optionally substitutedwith one or more halogen atoms; C3-C6 cycloalkyl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms; or phenyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms;

J represents J1 or J2:

X^(a) _(r) Y^(a) _(r) Z^(a) _(r) X^(b), Y^(b) and Z^(b) independentlyrepresent CH or a nitrogen atom;

R^(19a) and R^(19b) represent a hydrogen atom; C1-C6 alkyl optionallysubstituted with one or more halogen atoms; C2-C6 cyanoalkyl, C2-C6alkoxyalkyl optionally substituted with one or more halogen atoms; C2-C6alkenyl optionally substituted with one or more halogen atoms; C2-C6alkynyl optionally substituted with one or more halogen atoms; C3-C6cycloalkyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,and (2) C1-C6 alkyl optionally substituted with one or more halogenatoms; phenyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms, (5) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (6) C1-C6 alkylthio optionally substituted with oneor more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substitutedwith one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (9) C1-C6 alkylaminooptionally substituted with one or more halogen atoms, (10) C2-C6dialkylamino optionally substituted with one or more halogen atoms, (11)C2-C6 alkylcarbonyl optionally substituted with one or more halogenatoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; 5- to 6-membered heteroaryloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; C7-C9 phenylalkyl whosephenyl ring is optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms, (5) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (6) C1-C6 alkylthio optionally substituted with oneor more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substitutedwith one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (9) C1-C6 alkylaminooptionally substituted with one or more halogen atoms, (10) C2-C6dialkylamino optionally substituted with one or more halogen atoms, (11)C2-C6 alkylcarbonyl optionally substituted with one or more halogenatoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; or C7-C9 pyridinylalkylwhose pyridine ring is optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms;

R^(20a) and R^(20b) represent a halogen atom; cyano; nitro; thiocyanato;C1-C6 alkyl optionally substituted with one or more halogen atoms; C1-C6alkoxy optionally substituted with one or more halogen atoms; C2-C6cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substituted with one ormore halogen atoms; C2-C6 alkenyloxy optionally substituted with one ormore halogen atoms; C2-C6 alkynyloxy optionally substituted with one ormore halogen atoms; C1-C6 alkylthio optionally substituted with one ormore halogen atoms; C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms; C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms; phenyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 5- to 6-memberedheteroaryl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms; or phenoxy optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

p represents an integer of 0 to 3 (provided that, when p is an integerof 2 or 3, two or more R^(20a)s may be the same or different); and

q represents an integer of 0 to 3 (provided that, when q is an integerof 2 or 3, two or more R^(20b)s may be the same or different).

Furthermore this invention also contains a method of controlling aninvertebrate pest applying the present compound, an N-oxide thereof oran agricultural suitable salt thereof by contacting directly to a pest,or to a place where a pest inhabits. With includes the use of thepresent compound, an N-oxide thereof or an agricultural suitable saltthereof as active ingredient in a pesticidal composition.

A composition comprising of the present compound, an N-oxide thereof oran agricultural suitable salt thereof and at least one additionalcomponent selected from the group of surfactants, solid diluents andliquid diluents. This invention also includes a method for controllingan invertebrate pest by using the present compound, an N-oxide thereofor an agricultural suitable salt thereof as active ingredient in apesticidal composition and a biological active amount of at least oneadditional compound or agent. The invention also pertains to the use ofthe present compound, an N-oxide thereof or an agricultural suitablesalt thereof for manufacturing a pesticidal preparation.

BEST MODE FOR CARRYING OUT THE INVENTION

The compounds of this invention include every possible sterioisomer interms of enantiomers and diastereomers that can be formed from differentconfiguration at centers of asymmetry and different double bondconfiguration according to well-accepted definition of configurationisomers (Eliel, Ernest L., Wilien, Samuel H., Stereochemistry of OrganicCompounds, John Wiley & Son, 1994). The compounds of the invention canbe present as a mixture of the above-mentioned isomers, as a singlediastereomer or in an optically enriched form as active ingredients.Furthermore, the compounds of formula I of this invention can be presentas an N-oxide thereof or an agricultural suitable salt thereof. Allavailable nitrogen atoms whose lone pairs are not part of an aromaticmolecular H-orbital according to Hückel's rule can be oxidized at theirlone pairs to form N-oxides by using commonly known methods.Agricultural suitable salts of the compounds of this invention can beformed by addition of an inorganic or organic acid to the compound likefor example hydrochloric, hydrobromic, sulfuric, nitric and phosphoricacid as well as acetic, propionic, butyric, oxalic, malonic, tartaric,lactic, maleic, fumaric, citric, p-toluenesulfonic and salicylic acid.In case where compounds contain acidic moieties like carboxyl, sulfonylor phenol, salts can be formed by addition of an inorganic or organicbase like e.g. the hydroxides and carbonates of lithium, sodium,potassium, magnesium, calcium and barium or amines like ammonia,pyridine or triethylamine. The term ‘aromatic’ and ‘heteroaromatic’indicates that the carbocyclic or heterocyclic ring system is fullyunsaturated with a planar ring system allowing the ring systemsp-orbitals and optionally lone pair orbitals of heteroatoms, which areperpendicular to the ring plane to overlap to form a Π-molecular orbitalwith (4n+2) H-electrons according to Hückel's rule (n is 0 or a positiveinteger). The term ‘non-aromatic’ or ‘non-aromatic heterocyclic ringsystem’ refers to a ring system, which is fully or partial saturated orwhich is fully unsaturated but does not fulfill the requirements ofHückel's rule as mentioned above. The term ‘hetero’ in ‘heteroaromatic’,‘heterobicyclic’ and ‘non-aromatic heterocyclic ring’ denotes a ringsystem that contains at least one or more atom different from carbon,selected from the group of oxygen, nitrogen and sulfur. The heterocyclicring system can be attached at any available carbon or nitrogen atom byreplacement of hydrogen.

Hereinafter, the examples of the “substituents” are illustrated.

Examples of the 5- or 6-membered heteroaromatic ring system substitutedwith (R⁴), include E-1 to E-39 shown below. The heteroaromatic ringsystems E-1 to E-39 are attached with their upper right bond of anavailable carbon atom to the nitrogen atom of the —NR¹(C=A¹)J moiety.The hydrazide moiety —(C=A²)_(N)R²NR³Q is attached with the —(C=A²)carbon atom to an available carbon atom at the lower right bond of theexemplified ring systems E-1 to E-39.

Examples of the 8-, 9- or 10-membered fused heterobicyclic ring systemsubstituted with (R⁴), include E-40 to E-109 shown below. Substitutionof said heterobicyclic ring systems with substituents R⁴ is possible bysubstitution of carbon and nitrogen H-atoms on the aromatic ring systemsas well as on non-aromatic linking moieties (E-97-101, E-103, E-105,E-107-109). The heteroaromatic ring systems E-40 to E-109 are attachedwith their upper right bond of an available carbon atom to the nitrogenatom of the —NR¹(C=A¹)J moiety. The hydrazide moiety —(C=A²)_(N)R²NR³Qis attached with the —(C=A²) carbon atom to an available carbon atom atthe lower right bond of the exemplified ring systems E-40 to E-109.

Preferred ring systems include E-2, E-4, E-7, E-12, E-13, E-22, E-40 andE47; most preferred E-2 and E-4.

Examples of a halogen atom include a fluorine atom, a chlorine atom, abromine atom and an iodine atom.

Examples of C1-C6 alkyl optionally substituted with one or more halogenatoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl,sec-butyl, tert-butyl, pentyl and hexyl as well as fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl andpentafluoroethyl.

Examples of C1-C6 alkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (3) C1-C6 alkylthio optionally substituted with one ormore halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted withone or more halogen atoms, (5) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (6) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, and (7) C3-C6cycloalkyl optionally substituted with one or more halogen atoms includemethyl, trifluoromethyl, trichloromethyl, chloromethyl, dichloromethyl,fluoromethyl, difluoromethyl, methoxymethyl, ethoxymethyl,methylthiomethyl, ethylthiomethyl, methylsulfinylmethyl,methylsulfonylmethyl, dimethylaminomethyl, cyclopropylmethyl,cyclopentylmethyl, cyclohexylmethyl, ethyl, pentafluoroethyl, propyl,isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl.

Examples of C2-C6 cyanoalkyl include cyanomethyl and 2-cyanoethyl.

Examples of C2-C6 cyanoalkoxy include cyanomethoxy and 2-cyanoethoxy.

Examples of C1-C6 hydroxyalky include hydroxymethyl, 1-hydroxyethyl,2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl and2-hydroxy-isopropyl.

Examples of C1-C6 alkoxy optionally substituted with one or more halogenatoms include methoxy, trifluoromethoxy, ethoxy, 2,2,2-trifluoroethoxy,propyloxy, isopropyloxy, butoxy, isobutyloxy, sec-butoxy, tert-butoxy,pentyloxy and hexyloxy.

Examples of C2-C6 alkoxyalkyl optionally substituted with one or morehalogen atoms include methoxymethyl, ethoxymethyl, 2-methoxyethyl,2-ethoxyethyl and 2-isopropyloxyethyl.

Examples of C2-C6 alkoxyalkyloxy optionally substituted with one or morehalogen atoms include 2-(methoxy)ethoxy.

Examples of C2-C6 alkenyl optionally substituted with one or morehalogen atoms include 2-propenyl, 3-chloro-2-propenyl,2-chloro-2-propenyl, 3,3-dichloro-2-propenyl, 2-butenyl, 3-butenyl,2-methyl-2-propenyl, 3-methyl-2-butenyl, 2-pentenyl and 2-hexenyl aswell as polyenes like 1,3-pentadienyl and 2,4-hexadienyl and allpossible diastereomers.

Examples of C2-C6 alkenyloxy optionally substituted with one or morehalogen atoms include 2-propenyloxy, 3,3-dichloro-2-propenoxy and2-methyl-2-propenyloxy.

Examples of C2-C6 alkynyl optionally substituted with one or morehalogen atoms include 2-propynyl, 3-chloro-2-propynyl,3-bromo-2-propynyl, 2-butynyl and 3-butynyl as well as polyynes like2,5-hexadiynyl.

Examples of C2-C6 alkynyloxy optionally substituted with one or morehalogen atoms include 2-propynyloxy, 3-chloro-2-propynyloxy and2-butynyloxy.

Examples of C1-C6 alkylthio optionally substituted with one or morehalogen atoms include methylthio, trifluoromethylthio, ethylthio,propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio,tert-butylthio, pentylthio and hexylthio.

Examples of C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms include methylsulfinyl, trifluoromethylsulfinyl,ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl,isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyland hexylsulfinyl. The definition includes both sulfoxide enantiomers.

Examples of C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms include methylsulfonyl, trifluoromethylsulfonyl,ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl,isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyland hexylsulfonyl.

Examples of C1-C6 alkylamino include methylamino, ethylamino,n-propylamino, isopropylamino, n-butylamino, sec-butylamino,isobutylamino and tert-butylamino.

Examples of C1-C6 alkylamino optionally substituted with one or morehalogen atoms alkylamino include methylamino, ethylamino, n-propylamino,isopropylamino, n-butylamino, sec-butylamino, isobutylamino,tert-butylamino, 2-fluoroethyl amino, 2,2,2-trifluoroethyl amino,2,2,3,3,3-pentafluoropropyl amino and 2,2,3,3,4,4,4-heptafluoroamino.

Examples of C2-C8 dialkylamino include dimethylamino, diethylamino,ethylmethylamino, di-n-propylamino, diisopropylamino anddi-n-butylamino.

Examples of C2-C8 dialkylamino optionally substituted with one or morehalogen atoms include dimethylamino, diethylamino, ethylmethylamino,bis(2,2,2-trifluoroethyl)amino, di-n-propylamino, diisopropylamino anddi-n-butylamino.

Examples of C3-C6 cycloalkylamino include cyclopropyl amino,cyclobutylamino, cyclopentylamino and cyclohexylamino.

Examples of C2-C6 alkylcarbonyl include acetyl, propionyl, isobutyryland trimethylacetyl.

Examples of C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms include acetyl, trifluoroacetyl, trichloroacetyl,propionyl, pentafluoropropionyl, isobutyryl and trimethylacetyl.

Examples of C2-C6 alkoxycarbonyl include methoxycarbonyl,ethoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl.

Examples of C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms include methoxycarbonyl, ethoxycarbonyl,2-fluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl,2,2,2-trichloroethoxycarbonyl, isopropoxycarbonyl andtert-butoxycarbonyl.

Examples of C2-C6 alkylaminocarbonyl include methylaminocarbonyl,ethylaminocarbonyl, n-propylaminocarbonylcarbonyl,isopropylaminocarbonyl, n-butylaminocarbonyl, sec-butylaminocarbonyl,isobutylaminocarbonyl and tert-butylaminocarbonyl.

Examples of C2-C6 alkylaminocarbonyl optionally substituted with one ormore halogen atoms include methylaminocarbonyl, ethylaminocarbonyl,n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl,sec-butylaminocarbonyl, isobutylaminocarbonyl, tert-butylaminocarbonyl,2-fluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl,2,2,3,3,3-pentafluoropropylcarbonylaminocarbonyl and2,2,3,3,4,4,4-heptafluorobutylaminocarbonyl.

Examples of C3-C8 dialkylaminocarbonyl include dimethylaminocarbonyl anddiethylaminocarbonyl.

Examples of C4-C6 cycloalkylaminocarbonyl includecyclopropylaminocarbonyl, cyclobutylaminocarbonyl,cyclopentylaminocarbonyl and cyclohexylaminocarbonyl.

Examples of C3-C6 trialkylsilyl include trimthylsilyl, triethylsilyl andtertbutyldimethylsilyl.

Examples of C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms include cyclopropyl, 2-methylcyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl.

Examples of phenyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one ormore halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted withone or more halogen atoms, (11) C2-C6 alkenyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkynyl optionallysubstituted with one or more halogen atoms, (13) C3-C6 cycloalkyloptionally substituted with one or more halogen atoms, (14) C1-C6alkylthio optionally substituted with one or more halogen atoms, (15)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19)C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl include phenyl, 2-fluorophenyl, 3-fluorophenyl,4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,2-bromophenyl, 2-iodophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl,2-chloro-6-fluorophenyl, 2-chloro-4-fluorophenyl, 2-cyanophenyl,3-cyanophenyl, 4-cyanophenyl, 2-nitrophenyl, 3-nitrophenyl,4-nitrophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl,2-ethylphenyl, 2-isopropylphenyl, 2-tert-butylphenyl,2-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl,4-(trifluoromethyl)phenyl, 2-methoxyphenyl, 3-methoxyphenyl,4-methoxyphenyl, 2-ethoxyphenyl, 2-(trifluoromethoxy)phenyl,2-(methylthio)phenyl, 2-(methylsulfinyl)phenyl and2-(methylsulfonyl)phenyl.

Examples of benzyl optionally substituted with one or more substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8)C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9)C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms,(10) C2-C6 alkoxyalkyl optionally substituted with one or more halogenatoms, (11) C2-C6 alkenyl optionally substituted with one or morehalogen atoms, (12) C2-C6 alkynyl optionally substituted with one ormore halogen atoms, (13) C3-C6 cycloalkyl optionally substituted withone or more halogen atoms, (14) C1-C6 alkylthio optionally substitutedwith one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, (17) C1-C6alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20)C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include benzyl,2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl,3-chlorobenzyl, 4-chlorobenzyl, 2-bromobenzyl, 2-iodobenzyl,2,6-difluorobenzyl, 2,6-dichlorobenzyl, 2-chloro-6-fluorobenzyl,2-chloro-4-fluorobenzyl, 2-cyanobenzyl, 3-cyanobenzyl, 4-cyanobenzyl,2-nitrobenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 2-methylbenzyl,3-methylbenzyl, 4-methylbenzyl, 2-ethylbenzyl, 2-isopropylbenzyl,2-tert-butylbenzyl, 2-(trifluoromethyl)benzyl,3-(trifluoromethyl)benzyl, 4-(trifluoromethyl)benzyl, 2-methoxybenzyl,3-methoxybenzyl, 4-methoxybenzyl, 2-ethoxybenzyl,2-(trifluoromethoxy)benzyl, 2-(methylthio)benzyl,2-(methylsulfinyl)benzyl and 2-(methylsulfonyl)benzyl.

Examples of C7-C9 phenylalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6)C1-C6 alkyl optionally substituted with one or more halogen atoms, (7)C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with oneor more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substitutedwith one or more halogen atoms, (11) C2-C6 alkenyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkynyloptionally substituted with one or more halogen atoms, (13) C3-C6cycloalkyl optionally substituted with one or more halogen atoms, (14)C1-C6 alkylthio optionally substituted with one or more halogen atoms,(15) C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19)C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl include benzyl, 1-phenylethyl, 2-phenylethyl,2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-cyanobenzyl,3-cyanobenzyl, 4-cyanobenzyl, 2-nitrobenzyl, 3-nitrobenzyl,4-nitrobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl,2-(trifluoromethyl)benzyl, 3-(trifluoromethyl)benzyl,4-(trifluoromethyl)benzyl, 2-methoxybenzyl, 3-methoxybenzyl and4-methoxybenzyl.

Examples of phenoxy optionally substituted with one or more substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8)C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9)C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms,(10) C2-C6 alkoxyalkyl optionally substituted with one or more halogenatoms, (11) C2-C6 alkenyl optionally substituted with one or morehalogen atoms, (12) C2-C6 alkynyl optionally substituted with one ormore halogen atoms, (13) C3-C6 cycloalkyl optionally substituted withone or more halogen atoms, (14) C1-C6 alkylthio optionally substitutedwith one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, (17) C1-C6alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20)C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include phenoxy,2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2-cyanophenoxy,3-cyanophenoxy, 4-cyanophenoxy, 2-nitrophenoxy, 3-nitrophenoxy,4-nitrophenoxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy,2-(trifluoromethyl)phenoxy, 3-(trifluoromethyl)phenoxy,4-(trifluoromethyl)phenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy,4-methoxyphenoxy and 4-(trifluoromethoxy)phenoxy.

Examples of C7-C9 phenoxyalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms includephenoxymethyl, phenoxyethyl, 2-chlorophenoxymethyl,2-chlorophenoxyethyl, 3-chlorophenoxymethyl, 3-chlorophenoxyethyl,4-chlorophenoxymethyl, 4-chlorophenoxyethyl, 2-cyanophenoxymethyl,2-cyanophenoxyethyl, 3-cyanophenoxymethyl, 3-cyanophenoxyethyl,4-cyanophenoxymethyl, 4-cyanophenoxyethyl, 2-nitrophenoxymethyl,2-nitrophenoxyethyl, 3-nitrophenoxymethyl, 3-nitrophenoxyethyl,4-nitrophenoxymethyl, 4-nitrophenoxyethyl, 2-methylphenoxymethyl,2-methylphenoxyethyl, 3-methylphenoxymethyl, 3-methylphenoxyethyl,4-methylphenoxymethyl, 4-methylphenoxyethyl,2-(trifluoromethyl)phenoxymethyl, 2-(trifluoromethyl)phenoxyethyl,3-(trifluoromethyl)phenoxymethyl, 3-(trifluoromethyl)phenoxyethyl,4-(trifluoromethyl)phenoxymethyl, 4-(trifluoromethyl)phenoxyethyl,2-methoxyphenoxymethyl, 2-methoxyphenoxyethyl, 3-methoxyphenoxymethyl,3-methoxyphenoxyethyl, 4-methoxyphenoxymethyl, 4-methoxyphenoxyethyl,4-(trifluoromethoxy)phenoxymethyl and 4-(trifluoromethoxy)phenoxyethyl.

Examples of phenylcarbonyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6)C1-C6 alkyl optionally substituted with one or more halogen atoms, (7)C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with oneor more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substitutedwith one or more halogen atoms, (11) C2-C6 alkenyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkynyloptionally substituted with one or more halogen atoms, (13) C3-C6cycloalkyl optionally substituted with one or more halogen atoms, (14)C1-C6 alkylthio optionally substituted with one or more halogen atoms,(15) C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19)C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl include benzoyl, 2-fluorobenzoyl, 3-fluorobenzoyl,4-fluorobenzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl,2-bromobenzoyl, 2-iodobenzoyl, 2,6-difluorobenzoyl, 2,6-dichlorobenzoyl,2-chloro-6-fluorobenzoyl, 2-chloro-4-fluorobenzoyl, 2-cyanobenzoyl,3-cyanobenzoyl, 4-cyanobenzoyl, 2-nitrobenzoyl, 3-nitrobenzoyl,4-nitrobenzoyl, 2-methylbenzoyl, 3-methylbenzoyl, 4-methylbenzoyl,2-ethylbenzoyl, 2-isopropylbenzoyl, 2-tert-butylbenzoyl,2-(trifluoromethyl)benzoyl, 3-(trifluoromethyl)benzoyl,4-(trifluoromethyl)benzoyl, 2-methoxybenzoyl, 3-methoxybenzoyl,4-methoxybenzoyl, 2-ethoxybenzoyl, 2-(trifluoromethoxy)benzoyl,2-(methylthio)benzoyl, 2-(methylsulfinyl)benzoyl and2-(methylsulfonyl)benzoyl.

Examples of naphthyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms include 1-naphthyl and 2-naphthyl.

Examples of 5- or 6-membered heteroaromatic ring optionally substitutedwith one or more substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6)C1-C6 alkyl optionally substituted with one or more halogen atoms, (7)C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with oneor more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substitutedwith one or more halogen atoms, (11) C2-C6 alkenyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkynyloptionally substituted with one or more halogen atoms, (13) C3-C6cycloalkyl optionally substituted with one or more halogen atoms, (14)C1-C6 alkylthio optionally substituted with one or more halogen atoms,(15) C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19)C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl include 2-pyridinyl, 3-fluoro-2-pyridinyl,3-chloro-2-pyridinyl, 3-bromo-2-pyridinyl, 3-iodo-2-pyridinyl,3-methyl-2-pyridinyl, 3-trifluoromethyl-2-pyridinyl,3-methoxy-2-pyridinyl, 3-cyano-2-pyridinyl, 3-nitro-2-pyridinyl,3-pyridinyl, 2-chloro-3-pyridinyl, 4-chloro-3-pyridinyl, 4-pyridinyl,3-chloro-4-pyridinyl, 3,5-dichloro-4-pyridinyl, 2-pyrimidinyl,4-methyl-2-pyrimidinyl, 4,6-dimethyl-2-pyrimidinyl, 4-pyrimidinyl,5-chloro-4-pyrimidinyl, pyrazinyl, 3-methyl-2-pyrazinyl, 2-thiazolyl,1-methyl-5-pyrazolyl, 4-chloro-1-methyl-5-pyrazolyl,4-chloro-1,3-dimethyl-5-pyrazolyl and 4-chloro-5-methyl-3-isooxazolyl.

Examples of 3- to 8-membered non-aromatic heterocyclic ring optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms include pyrrolidin-1-yl,piperidino, 3,5-dimethylpiperidino, hexamethyleneimin-1-yl,heptamethyleneimin-1-yl, morpholino, 2,6-dimethylmorpholino,thiomorpholin-4-yl, 4-methylpiperazin-1-yl,4-(ethoxycarbonyl)piperazin-1-yl and 4-phenylpiperazin-1-yl.

Examples of C7-C9 pyridinylalkyl whose pyridine ring is optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, (5) C1-C6alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms include 2-pyridinylmethyl, 3-pyridinylmethyl,4-pyridinylmethyl, 3-chloro-2-pyridinylmethyl and2-chloro-3-pyridinylmethyl.

Examples of R² and R³ are taken together with the two nitrogen atoms towhich they are attached to form a 5- to 8-membered ring containing twonitrogen atoms, one or more CH₂ or C(═O), and optionally one or two ringmembers selected from the group consisting of (1) an oxygen atom, (2) asulfur atom, (3) S(═O), (4) S(═O)₂ and (4) NR^(a) are shown below asring T. Said ring at the carbon atoms is substituted by one or moreindependent G⁶, which represents a halogen atom, C1-C6 alkyl optionallysubstituted with one or more halogen atoms, and C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms. Further ringmembers from nitrogen —NR^(a)— (not included the two contiguous linkingnitrogen atoms) with free valences can be substituted by R^(a) which isselected from the group consisting of C1-C6 alkyl optionally substitutedwith one or more halogen atoms, C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, or a phenyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of a halogen atom, cyano, nitro, C1-C6 alkyl optionallysubstituted with one or more halogen atoms, C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, C1-C6 alkylthio optionallysubstituted with one or more halogen atoms, C1-C6 alkylsulfinyloptionally substituted with one or more halogen atoms, C1-C6alkylsulfonyl optionally substituted with one or more halogen atoms,C1-C6 alkylamino optionally substituted with one or more halogen atoms,C2-C6 dialkylamino optionally substituted with one or more halogenatoms, C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, C2-C6 alkoxycarbonyl optionally substituted with one ormore halogen atoms, C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms.

Said ring systems T are connected with the left upper nitrogen atom fromthe two contiguous linking nitrogen atoms via —(C=A²)- moiety with thering system E, which represents, a 5- or 6-membered heteroaromatic ringsystem or a 8-, 9- or 10-membered fused heterobicyclic ring system.

The substituent Q represents Q1, Q2, Q3, Q4, Q5 or Q6:

A³¹, A³², A³³ and A³⁴ represent an oxygen atom, or a sulfur atom; mrepresents an integer of 0 to 2. Substituents R⁶ to R¹³ are selected asexplained above in the summary of the invention.

J represents J1 or J2. Examples for said ring J1 and J2 are shown belowas J-1.1 to J-1.8 and J-2.1 to J-2.8. The ring systems J-1.1 to J-1.8and J-2.1 to J-2.8 are connected with their very left carbon atom viathe —(C=A¹)- group of the —NR¹(C=A¹)J moiety with the ring system E,which represents, a 5- or 6-membered heteroaromatic ring system or a 8-,9- or 10-membered fused heterobicyclic ring system. One nitrogen atom issubstituted by R^(19a) (J1) or R^(19b) (J2) Ring carbon atoms areoptionally substituted by 1 to 3 substituents R^(20a) (J1) or R^(20b)(J2) provided that, when 2 or 3 substituents R^(20a) (J1) or R^(20b)(J2) are present, two or more R^(20a)'s and R^(20b)'s may be the same ordifferent. Substituents R^(19a)(J1), R^(19b)(J2), R^(20a) (J1) andR^(20b)(J2) are selected as explained above in the summary of theinvention.

Preferred ring systems include J-1.1, J-1.2, J-2.1 and J-2.2; mostpreferred J-1.1 and J-1.2.

Detailed examples of the group represented by J1 include1-phenylpyrazol-5-yl, 1-(2-chlorophenyl)pyrazol-5-yl,1-(2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)pyrazol-5-yl, a3-fluoro-1-phenylpyrazol-5-yl, 1-(2-chlorophenyl)-3-fluoropyrazol-5-yl,3-fluoro-1-(2-pyridinyl)pyrazol-5-yl,3-fluoro-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,3-chloro-1-phenylpyrazol-5-yl, 3-chloro-1-(2-chlorophenyl)pyrazol-5-yl,3-chloro-1-(2-pyridinyl)pyrazol-5-yl,3-chloro-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,3-bromo-1-phenylpyrazol-5-yl, 3-bromo-1-(2-chlorophenyl)pyrazol-5-yl,3-bromo-1-(2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,3-iodo-1-phenylpyrazol-5-yl, 3-iodo-1-(2-chlorophenyl)pyrazol-5-yl,3-iodo-1-(2-pyridinyl)pyrazol-5-yl,3-iodo-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,3-methyl-1-phenylpyrazol-5-yl, 1-(2-chlorophenyl)-3-methylpyrazol-5-yl,3-methyl-1-(2-pyridinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-methylpyrazol-5-yl,1-phenyl-3-(trifluoromethyl)pyrazol-5-yl,1-(2-chlorophenyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,3-chloro-1-methylpyrazol-5-yl, 3-chloro-1-ethylpyrazol-5-yl,3-chloro-1-isopropylpyrazol-5-yl, 1-tert-butyl-3-chloropyrazol-5-yl,3-chloro-1-(3-fluoro-2-pyridinyl)pyrazol-5-yl,1-(3-bromo-2-pyridinyl)-3-chloropyrazol-5-yl,3-chloro-1-(3-iodo-2-pyridinyl)pyrazol-5-yl,3-chloro-1-(3-methyl-2-pyridinyl)pyrazol-5-yl,3-chloro-1-(3-trifluoromethyl-2-pyridinyl)pyrazol-5-yl,3-chloro-1-(3-methoxy-2-pyridinyl)pyrazol-5-yl,3-chloro-1-(3-cyano-2-pyridinyl)pyrazol-5-yl,3-chloro-1-(3-nitro-2-pyridinyl)pyrazol-5-yl,3-bromo-1-methylpyrazol-5-yl, 3-bromo-1-ethylpyrazol-5-yl,3-bromo-1-isopropylpyrazol-5-yl, 3-bromo-1-tert-butylpyrazol-5-yl,3-bromo-1-(3-fluoro-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-bromo-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-iodo-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-methyl-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-trifluoromethyl-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-methoxy-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-cyano-2-pyridinyl)pyrazol-5-yl,3-bromo-1-(3-nitro-2-pyridinyl)pyrazol-5-yl,1-methyl-3-(trifluoromethyl)pyrazol-5-yl,1-ethyl-3-(trifluoromethyl)pyrazol-5-yl,1-isopropyl-3-(trifluoromethyl)pyrazol-5-yl,1-tert-butyl-3-(trifluoromethyl)pyrazol-5-yl,1-(3-fluoro-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-bromo-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-iodo-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-methyl-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-trifluoromethyl-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-methoxy-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-cyano-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-nitro-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-ethylpyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-isopropylpyrazol-5-yl,3-tert-butyl-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(methylthio)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(ethylthio)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(isopropylthio)pyrazol-5-yl,3-tert-butylthio-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(methylsulfinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(ethylsulfinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(isopropylsulfinyl)pyrazol-5-yl,3-tert-butylsulfinyl-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(methylsulfonyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(ethylsulfonyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(isopropylsulfonyl)pyrazol-5-yl,3-tert-butylsulfonyl-1-(3-chloro-2-pyridinyl)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-(2,2,2-trifluoroethoxy)pyrazol-5-yl,1-(3-chloro-2-pyridinyl)-3-cyanopyrazol-5-yl,1-(2-chlorophenyl)pyrrol-2-yl, 1-(3-chloro-2-pyridinyl)pyrrol-2-yl,4-chloro-1-(2-chlorophenyl)pyrrol-2-yl,4-chloro-1-(3-chloro-2-pyridinyl)pyrrol-2-yl,5-chloro-1-(2-chlorophenyl)pyrrol-2-yl,5-chloro-1-(3-chloro-2-pyridinyl)pyrrol-2-yl,1-(2-chlorophenyl)-4,5-dichloropyrrol-2-yl,1-(3-chloro-2-pyridinyl)-4,5-dichloropyrrol-2-yl,4-bromo-1-(2-chlorophenyl)pyrrol-2-yl,4-bromo-1-(3-chloro-2-pyridinyl)pyrrol-2-yl,5-bromo-1-(2-chlorophenyl)pyrrol-2-yl,5-bromo-1-(3-chloro-2-pyridinyl)pyrrol-2-yl,1-(2-chlorophenyl)-4,5-dibromopyrrol-2-yl,1-(3-chloro-2-pyridinyl)-4,5-dibromopyrrol-2-yl,1-(2-chlorophenyl)-4-iodopyrrol-2-yl,1-(3-chloro-2-pyridinyl)-4-iodopyrrol-2-yl,1-(2-chlorophenyl)-5-iodopyrrol-2-yl,1-(3-chloro-2-pyridinyl)-5-iodopyrrol-2-yl,1-(2-chlorophenyl)-4,5-diiodopyrrol-2-yl,1-(3-chloro-2-pyridinyl)-4,5-diiodopyrrol-2-yl,1-(2-chlorophenyl)-4-(trifluoromethyl)pyrrol-2-yl,1-(3-chloro-2-pyridinyl)-4-(trifluoromethyl)pyrrol-2-yl,1-(2-chlorophenyl)-5-(trifluoromethyl)pyrrol-2-yl,1-(3-chloro-2-pyridinyl)-5-(trifluoromethyl)pyrrol-2-yl,1-(2-chlorophenyl)imidazol-2-yl, 1-(3-chloro-2-pyridinyl)imidazol-2-yl,4-chloro-1-(2-chlorophenyl)imidazol-2-yl,4-chloro-1-(3-chloro-2-pyridinyl)imidazol-2-yl,4-bromo-1-(2-chlorophenyl)imidazol-2-yl,4-bromo-1-(3-chloro-2-pyridinyl)imidazol-2-yl,1-(2-chlorophenyl)-4-(trifluoromethyl)imdazol-2-yl,1-(3-chloro-2-pyridinyl)-4-(trifluoromethyl)imidazol-2-yl,1-(2-chlorophenyl)-1,2,4-triazol-5-yl,1-(3-chloro-2-pyridinyl)-1,2,4-triazol-5-yl,3-chloro-1-(2-chlorophenyl)-1,2,4-triazol-5-yl,3-chloro-1-(3-chloro-2-pyridinyl)-1,2,4-triazol-5-yl,3-bromo-1-(2-chlorophenyl)-1,2,4-triazol-5-yl,3-bromo-1-(3-chloro-2-pyridinyl)-1,2,4-triazol-5-yl,1-(2-chlorophenyl)-3-(trifluoromethyl)-1,2,4-triazol-5-yl and1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1,2,4-triazol-5-yl.

Examples of the group represented by J2 include1-methyl-3-phenylpyrazol-4-yl, 3-(2-chlorophenyl)-1-methylpyrazol-4-yl,1-methyl-3-(2-pyridinyl)pyrazol-4-yl,3-(3-chloro-2-pyridinyl)-1-methylpyrazol-4-yl,1-methyl-5-phenylpyrazol-4-yl, 5-(2-chlorophenyl)-1-methylpyrazol-4-yl,1-methyl-5-(2-pyridinyl)pyrazol-4-yl,5-(3-chloro-2-pyridinyl)-1-methylpyrazol-4-yl,3-phenyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,3-(2-chlorophenyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,3-(2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,3-(3-chloro-2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,5-phenyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,5-(2-chlorophenyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,5-(2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,5-(3-chloro-2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl,1-(difluoromethyl)-3-phenylpyrazol-4-yl,3-(2-chlorophenyl)-1-(difluoromethyl)pyrazol-4-yl,1-(difluoromethyl)-3-(2-pyridinyl)pyrazol-4-yl,3-(3-chloro-2-pyridinyl)-1-(difluoromethyl)pyrazol-4-yl,1-(difluoromethyl)-5-phenylpyrazol-4-yl,5-(2-chlorophenyl)-1-(difluoromethyl)pyrazol-4-yl,1-(difluoromethyl)-5-(2-pyridinyl)pyrazol-4-yl,5-(3-chloro-2-pyridinyl)-1-(difluoromethyl)pyrazol-4-yl,3-(2-chlorophenyl)-1-ethylpyrazol-4-yl,3-(3-chloro-2-pyridinyl)-1-ethylpyrazol-4-yl,5-(2-chlorophenyl)-1-ethylpyrazol-4-yl,5-(3-chloro-2-pyridinyl)-1-ethylpyrazol-4-yl,3-(2-chlorophenyl)-1-isopropylpyrazol-4-yl,3-(3-chloro-2-pyridinyl)-1-isopropylpyrazol-4-yl,5-(2-chlorophenyl)-1-isopropylpyrazol-4-yl,5-(3-chloro-2-pyridinyl)-1-isopropylpyrazol-4-yl,3-(2-chlorophenyl)-1-tert-butylpyrazol-4-yl,3-(3-chloro-2-pyridinyl)-1-tert-butylpyrazol-4-yl,5-(2-chlorophenyl)-1-tert-butylpyrazol-4-yl and5-(3-chloro-2-pyridinyl)-1-tert-butylpyrazol-4-yl.

Hereinafter, preferred embodiments of the present invention areillustrated.

Preferred compounds are:

Preferred Compound 1: The compound according to the present compound, anN-oxide thereof or suitable salt thereof, wherein E is a 5- or6-membered heteroaromatic ring.

Preferred Compound 2: The compound according to the Preferred Compound1, wherein

A¹ and A² are oxygen atoms; and

R¹ is a hydrogen atom or alkyl optionally substituted with one or morehalogen atoms.

Preferred Compound 3: The compound according to the Preferred Compound2, wherein J is J-1.1, J-1.2, J-2.1, J-2.2 or J-2.3:

wherein

R^(19a) and R^(19b) represent a hydrogen atom; C1-C6 alkyl optionallysubstituted with one or more halogen atoms; C3-C6 cycloalkyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

R^(20a) and R^(20b) represent a halogen atom, cyano, C1-C6 alkyloptionally substituted with one or more halogen atoms, C1-C6 alkoxyoptionally substituted with one or more halogen atoms, C2-C6cyanoalkyloxy, C2-C6 alkoxyalkyloxy optionally substituted with one ormore halogen atoms, C2-C6 alkenyloxy optionally substituted with one ormore halogen atoms, C1-C6 alkylthio optionally substituted with one ormore halogen atoms, C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms;

or phenyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

or phenoxy optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms;

p represents an integer of 0 to 3; and

q represents an integer of 0 to 3 (provided that, when p is an integerof 2 or 3, two or more R^(20a)'s may be the same or different and, whenq is an integer of 2 or 3, two or more R^(20b)'s may be the same ordifferent).

Preferred Compound 4: The compound according to the present compound, anN-oxide thereof or suitable salt thereof, wherein

Q is Q1;

A³¹ is oxygen; and

R⁶ represents a hydrogen atom; C1-C6 alkyl optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, (2) C1-C6 alkoxy optionally substituted with oneor more halogen atoms, (3) C1-C6 alkylthio optionally substituted withone or more halogen atoms, (4) C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, (6) C2-C6dialkylamino optionally substituted with one or more halogen atoms, and(7) C3-C6 cycloalkyl optionally substituted with one or more halogenatoms;

C3-C6 cycloalkyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,and (2) C1-C6 alkyl optionally substituted with one or more halogenatoms;

phenyl optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

3- to 8-membered non-aromatic heterocyclic optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted withone or more halogen atoms;

or C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ringoptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms and (5) C1-C6 alkoxy optionally substituted with one or morehalogen atoms.

Preferred Compound 5: The compound according to the Preferred Compound4, wherein A¹ and A² are oxygen atoms.

Preferred Compound 6: The compound according to the present compound, anN-oxide thereof or suitable salt thereof, wherein

Q is Q2;

A³² is oxygen; and

R⁷ is C1-C6 alkyl optionally substituted with one or more halogen atoms;C2-C6 alkenyl optionally substituted with one or more halogen atoms;C3-C6 cycloalkyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,and (2) C1-C6 alkyl optionally substituted with one or more halogenatoms;

phenyl optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl (8) C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, (9) C1-C6alkylamino optionally substituted with one or more halogen atoms, (10)C2-C6 dialkylamino optionally substituted with one or more halogenatoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with oneor more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionallysubstituted with one or more halogen atoms and (14) C3-C6dialkylaminocarbonyl optionally substituted with one or more halogenatoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

or C7-C9 phenylalkyl whose ring moiety is optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms.

Preferred Compound 7: The compound according to the Preferred Compound6, wherein A¹ and A² are oxygen atoms.

Preferred Compound 8: The compound according to the present compound, anN-oxide thereof or suitable salt thereof, wherein

Q is Q4;

A³⁴ is oxygen; and

R⁹ and R¹⁰ independently represent a hydrogen atom; C1-C6 alkyloptionally substituted with one or more halogen atoms; C3-C6 cycloalkyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, and (2) C1-C6alkyl optionally substituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl (13) C2-C6 alkylaminocarbonyl optionallysubstituted with one or more halogen atoms and (14) C3-C6dialkylaminocarbonyl optionally substituted with one or more halogenatoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

or C7-C9 phenylalkyl whose ring moiety is optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms.

Preferred Compound 9: The compound according to the Preferred Compound8, wherein A¹ and A² are oxygen atoms.

Preferred Compound 10: A hydrazide compound represented by the formula(II-1) or (II-2),

wherein

X^(a) represents a nitrogen atom or CR^(20aax);

Y and Z represent independently a nitrogen atom or CR^(4b), but not Yand Z are CR^(4b) at the same time;

R¹ represets a hydrogen atom or C1-C6 alkyl optionally substituted withone or more halogen atoms;

R² and R³ independently represent a hydrogen atom, C1-C6 alkyloptionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl,C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionally substituted with one ormore halogen atoms, C2-C6 alkenyl optionally substituted with one ormore halogen atoms, C2-C6 alkynyl optionally substituted with one ormore halogen atoms, C3-C6 cycloalkyl optionally substituted with one ormore halogen atoms, C1-C6 alkylthio optionally substituted with one ormore halogen atoms, C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms, C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C4-C6cycloalkylaminocarbonyl, or C3-C6 trialkylsilyl;

or represents phenyl, C7-C9 phenylalkyl or phenylcarbonyl: each saidphenyl ring optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl; or

R² and R³ are taken together with the two nitrogen atoms to which theyare attached to form a 5- to 8-membered ring containing two nitrogenatoms, one or more CH₂ or C(═O), and optionally one or two ring membersselected from the group consisting of (1) an oxygen atom, (2) a sulfuratom, (3) S(═O), (4) S(═O)₂ and (4) NR^(a) (wherein R^(a) representsC1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6alkoxycarbonyl optionally substituted with one or more halogen atoms, ora phenyl optionally substituted with one or more independentsubstituents from (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, (5) C1-C6alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms;

and wherein the ring at the carbon atoms is optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, (2) C1-C6 alkyl optionally substituted with oneor more halogen atoms, and (3) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms;

R^(4a), R^(4b) and R^(4c) independently represent a halogen atom, cyano,nitro, hydroxyl, carboxyl, C1-C6 alkyl optionally substituted with oneor more halogen atoms, C2-C6 alkoxy optionally substituted with one ormore halogen atoms, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, C2-C6 alkenyl optionallysubstituted with one or more halogen atoms, C2-C6 alkynyl optionallysubstituted with one or more halogen atoms, C3-C6 cycloalkyl optionallysubstituted with one or more halogen atoms, C1-C6 alkylthio optionallysubstituted with one or more halogen atoms, C1-C6 alkylsulfinyloptionally substituted with one or more halogen atoms, C1-C6alkylsulfonyl optionally substituted with one or more halogen atoms,C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C3-C6 trialkylsilyl;

or represents independently phenyl, benzyl, phenoxy, or 5- or 6-memberedheteroaromatic ring, each ring optionally substituted with one or moresubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl;

M is a hydrogen atom; C1-C6 alkyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (3) C1-C6 alkylthio optionally substituted with one ormore halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted withone or more halogen atoms, (5) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (6) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, and (7) C3-C6cycloalkyl optionally substituted with one or more halogen atoms; C1-C6alkoxy optionally substituted with one or more halogen atoms; C1-C6alkylthio optionally substituted with one or more halogen atoms; C1-C6alkylamino; C2-C8 dialkylamino;

phenyl, C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ringoptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, and (5) C1-C6 alkoxy optionally substituted with one or morehalogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

or 3- to 8-membered non-aromatic heterocyclic ring optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms;

R^(19ax) represents a hydrogen atom; C1-C6 alkyl optionally substitutedwith one or more halogen atoms; C2-C6 cyanoalkyl; C2-C6 alkoxyalkyloptionally substituted with one or more halogen atoms; C2-C6 alkenyloptionally substituted with one or more halogen atoms; C2-C6 alkynyloptionally substituted with one or more halogen atoms; C3-C6 cycloalkyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, and (2) C1-C6alkyl optionally substituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms;

C7-C9 phenylalkyl whose phenyl ring is optionally substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms;

or C7-C9 pyridinylalkyl whose pyridine ring is optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms, (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; and

R^(20ax), R^(20ay) and R^(20az) represent a halogen atom; cyano; nitro;thiocyanato; C1-C6 alkyl optionally substituted with one or more halogenatoms; C1-C6 alkoxy optionally substituted with one or more halogenatoms; C2-C6 cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substitutedwith one or more halogen atoms; C2-C6 alkenyloxy optionally substitutedwith one or more halogen atoms; C2-C6 alkynyloxy optionally substitutedwith one or more halogen atoms; C1-C6 alkylthio optionally substitutedwith one or more halogen atoms; C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms; C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms; phenyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

or phenoxy optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms.

Preferred Compound 11: The compound according to the Preferred Compound10, wherein

R¹ is a hydrogen atom;

R² is a hydrogen atom or C1-C6 alkyl optionally substituted with one ormore halogen atoms;

R³ is a hydrogen atom, C1-C6 alkyl optionally substituted with one ormore halogen atoms or C2-C6 alkoxycarbonyl;

R^(4a) is a halogen atom or C1-C6 alkyl optionally substituted with oneor more halogen atoms;

R^(4c) is a hydrogen atom, a halogen atom, cyano or C1-C6 alkyloptionally substituted with one or more halogen atoms; R^(19a) is

wherein

X^(b) is a nitrogen atom or CR^(21a);

R^(20ax) and R^(23ay) are independently a hydrogen atom, a halogen atom,C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6alkoxy optionally substituted with one or more halogen atoms or C1-C6alkylthio optionally substituted with one or more halogen atoms;

R^(20az) is a hydrogen atom; and

R^(21a), R^(21b) and R^(21c) are independently selected from the groupconsisting of a hydrogen atom, a halogen atom or C1-C6 alkyl optionallysubstituted with one or more halogen atoms.

Preferred Compound 12: The compound according to the Preferred Compound11, wherein

X^(a) and X^(b) are nitrogen atoms;

Y is CH; and

Z is a nitrogen atom.

Preferred Compound 13: The compound according to the Preferred Compound11, wherein

X^(a) and X^(b) are nitrogen atoms;

Y is a nitrogen atom; and

Z is CH.

Preferred Compound 14: The compound according to the Preferred Compound11, wherein R^(4b) is a hydrogen atom.

Preferred Compound 15: The compound according to the Preferred Compound14, wherein M is a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, amino,C1-C6 alkylamino or C2-C8 dialkylamino.

Preferred Compound 16: The compound according to the Preferred Compound15, wherein

R² is a hydrogen atom, methyl or ethyl;

R³ is a hydrogen atom, methyl, ethyl or methoxycarbonyl;

R^(4a) is methyl, chloro, bromo or iodo;

R^(4c) is hydrogen, fluoro, chloro, bromo, iodo or cyano;

R^(20ay) is chloro, bromo, iodo, trifluoromethyl or pentafluoroethoxy;

R^(22b) is a hydrogen atom;

R^(22c) is chloro or bromo; and

M is hydrogen, methoxy, ethoxy, methylamino or dimethylamino.

Preferred Compound 17: The compound of the Preferred Compound 16,wherein

R² is a hydrogen atom;

R³ is methyl or ethyl; and

M is a hydrogen atom.

Preferred Compound 18: The compound of the Preferred Compound 17,wherein

R² and R³ are independently hydrogen, methyl or ethyl; and

M is methoxy or ethoxy.

Preferred Compound 19: A hydrazide compound represented by the formula(II-1),

X^(a), Y, Z, R¹, R², R³, R^(4a), R^(4b), R^(4c), M, R^(19ax), R^(20ax),R^(20ay), and R^(20az) are described above.

Preferred Compound 20: The compound according to the Preferred Compound19, wherein

R¹ is a hydrogen atom;

R² is a hydrogen atom or C1-C6 alkyl optionally substituted with one ormore halogen atoms;

R³ is a hydrogen atom, C1-C6 alkyl optionally substituted with one ormore halogen atoms or C2-C6 alkoxycarbonyl;

R^(4a) is a halogen atom or C1-C6 alkyl optionally substituted with oneor more halogen atoms;

R^(4c) is a hydrogen atom, a halogen atom, cyano or 1-C6 alkyloptionally substituted with one or more halogen atoms;

R^(19a) is

wherein

X^(b) is a nitrogen atom or CR^(21a);

R^(20ax) and R^(23ay) are independently a hydrogen atom, a halogen atom,C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6alkoxy optionally substituted with one or more halogen atoms or C1-C6alkylthio optionally substituted with one or more halogen atoms;

R^(20 az) is a hydrogen atom; and

R^(21a), R^(21b) and R^(21c) are independently selected from the groupconsisting of a hydrogen atom, a halogen atom or C1-C6 alkyl optionallysubstituted with one or more halogen atoms.

Preferred Compound 21: The compound according to the Preferred Compound20, wherein

X^(a) and X^(b) are nitrogen atoms;

Y is CH; and

Z is a nitrogen atom.

Preferred Compound 22: The compound according to the Preferred Compound20, wherein

X^(a) and X^(b) are nitrogen atoms;

Y is a nitrogen atom; and

Z is CH.

Preferred Compound 23: The compound according to the Preferred Compound20, wherein R^(4b) is a hydrogen atom.

Preferred Compound 24: The compound according to the Preferred Compound23, wherein M is a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, amino,C1-C6 alkylamino or C2-C8 dialkylamino.

Preferred Compound 25: The compound according to the Preferred Compound24, wherein

R² is a hydrogen atom, methyl or ethyl;

R³ is a hydrogen atom, methyl, ethyl or methoxycarbonyl;

R^(4a) is methyl, chloro, bromo or iodo;

R^(4c) is hydrogen, fluoro, chloro, bromo, iodo or cyano;

R^(20ay) is chloro, bromo, iodo, trifluoromethyl or pentafluoroethoxy;

R^(22b) is a hydrogen atom;

R^(22c) is chloro or bromo; and

M is hydrogen, methoxy, ethoxy, methylamino or dimethylamino.

Preferred Compound 26: The compound of the Preferred Compound 25,wherein

R² is a hydrogen atom;

R³ is methyl or ethyl; and

M is a hydrogen atom.

Preferred Compound 27: The compound of the Preferred Compound 26,wherein

R² and R³ are independently hydrogen, methyl or ethyl; and

M is methoxy or ethoxy.

This invention further pertains to:

A pesticide comprising the present compound or an N-oxide thereof orsuitable salt thereof as an active ingredient.

A method of controlling a pest which comprises applying the presentcompound, an N-oxide thereof or suitable salt thereof directly to apest, or to a place where a pest inhabits.

Use of the present compound, an N-oxide thereof or suitable salt thereoffor controlling a pest.

Use of the present compound, an N-oxide thereof or suitable salt thereoffor manufacturing a pesticidal preparation.

Hereinafter, a process for producing the present compound will beexplained.

The present compound can be produced, for example, by the followingProcess A-1 to Process C-1.

Process A-1

Among the present compounds, a compound represented by the formula (1):

wherein R¹, R², R³, R⁴, A¹, A², J and n are as defined above;

E represents, together with the two contiguous linking carbon atoms, a5- or 6-membered heteroaromatic ring system or a 8-, 9- or 10-memberedfused heterobicyclic ring system;

Q′ represents a group selected from the group consisting of Q1 to Q6(provided that the compound wherein Q′ is Q4, and R⁸ and R⁹ are ahydrogen atom is excluded) (hereinafter, referred to as the compound(I)) can be produced by reacting a compound represented by the formula(2):

wherein R¹, R², R³, R⁴, A¹, A², J and n are as defined above(hereinafter, referred to as the compound (2)), and a compoundrepresented by the formula (3):L¹-Q′  (3)wherein Q′ is as defined above; and

L¹ represents a halogen atom or a Q′-O— (provided that the case where Q′is Q4, and R⁸ and R⁹ are a hydrogen atom is excluded) (hereinafter,referred to as the compound (3)).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methlpyrrolidone,1,3-dimethyl-2-imidadzolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (3) to be used in the reaction is usually 1to 2 mols per 1 mol of the compound (2).

The reaction is performed in the presence of a base, if necessary.Examples of the base include nitrogen-containing heterocyclic compoundssuch as pyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene(DBN), and the like, tertiary amines such as triethylamine,N,N-diisopropylethylamine, and the like, and inorganic bases such aspotassium carbonate, sodium hydride, and the like. The amount of thebase when the reaction is performed in the presence of the base isusually 1 to 2 mols per 1 mol of the compound (2), while the base may beused in an excess amount in case that the base used is liquid under thereaction conditions such as pyridine, and the like.

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-i) can be isolated bypouring the reaction mixture into water and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (1-i) may be further purified byrecrystallization, chromatography, or the like.

Process A-2

Among the present compounds, a compound represented by the formula(I-ii):

wherein R¹, R², R³, R⁴, A¹, A², A³⁴, J and n are as defined above, andR^(9a) represents C1-C6 alkyl optionally substituted with at least onehalogen atom; C2-C6 alkoxyalkyl optionally substituted with at least onehalogen atom; C2-C6 alkenyl optionally substituted with at least onehalogen atom; 3-C6 alkynyl optionally substituted with at least onehalogen atom; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom and (2) C1-C6 alkyl group; a phenyl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom (2) cyano group, (3) nitro group, (4)C1-C6 alkyl optionally substituted with at least one halogen atom, (5)C1-C6 alkoxy optionally substituted with at least one halogen atom, (6)C1-C6 alkylthio optionally substituted with at least one halogen atom,(7) C1-C6 alkylsulfinyl optionally substituted with at least one halogenatom, (8) C1-C6 alkylsulfonyl optionally substituted with at least onehalogen atom, (9) C2-C6 dialkylamino optionally substituted with atleast one halogen atom and (10) C2-C6 alkoxycarbonyl optionallysubstituted with at least one halogen atom; 5- to 6-membered heteroaryloptionally substituted with one or more independent substituentsselected from the group consisting of (1) halogen atom, (2) cyano group,(3) nitro group, (4) C1-C6 alkyl optionally substituted with at leastone halogen atom and (5) C1-C6 alkoxy optionally substituted with atleast one halogen atom; or C7-C9 phenylaklyl whose benzene ring moietymay be substituted with one or more independent substituents selectedfrom the group consisting of (1) a halogen atom, (2) cyano group, (3)nitro group, (4) C1-C6 alkyl optionally substituted with at least onehalogen atom and (5) C1-C6 alkoxy optionally substituted with at leastone halogen atom (hereinafter, referred to as the compound (1-ii)) canbe produced by reacting the compound (2) with a compound represented bythe formula (4):A34=C═N—R^(9a)  (4)wherein A³⁴ and R^(9a) are as defined above (hereinafter, referred to asthe compound (4)).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (4) used in the reaction is usually 1 to 2mols per 1 mol of the compound (2).

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is a usually a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-ii) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (1-ii) may be further purified byrecrystallization, chromatography, or the like.

Process A-3

Among the present compounds, a compound represented by the formula(1-iii):

wherein R¹, R², R³, R⁴, A″ A², A³⁴, J and n are as defined above(hereinafter, referred to as the compound (I-iii)) can be produced byreacting the compound (2) and a cyanate or a thiocyanate.

The reaction is performed in the presence of a solvent. Examples of thesolvent used in the reaction include acids such as organic acids such asacetic acids, and the like and mineral acids such as hydrochloric acid,and the like, as well as a mixture of these acids and water, chloroform,or the like.

The amount of the cyanate or the thiocyanate used in the reaction isusually 1 to 2 mols per 1 mol of the compound (2).

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 24 hours.

Examples of the cyanate or the thiocyanate include potassium cyanate,sodium cyanate, ammonium cyanate, potassium thiocyanate, sodiumthiocyanate and ammonium thiocyanate.

After completion of the reaction, the compound (I-iii) can be isolatedby pouring the reaction mixture into water and extracting the mixturewith an organic solvent, or collecting a deposited precipitate byfiltration. The isolated Compound (I-iii) may be further purified byrecrystallization, chromatography, or the like.

Process B-1

The present compound can be produced by reacting a compound representedby the formula (6):

wherein R¹, R², R³, R⁴, A², Q and n are as defined above (hereinafter,referred to as Compound (6)) and a compound represented by the formula(7):

wherein A¹ and J are as define above, and L² represents a halogen atom(hereinafter, referred to as the compound (7)).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent used in the reaction include ethers such as1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (7) used in the reaction is usually 1 to 2mols per 1 mol of the compound (6).

The reaction is performed in the presence of a base, if necessary.Examples of the base include nitrogen-containing heterocyclic compoundssuch as pyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazadicyclo[4,3,0]5-nonene(DBN), and the like, tertiary amines such as triethylamine,N,N-diisopropylethylamine, and the like, and inorganic bases such aspotassium carbonate, sodium hydride, and the like. The amount of thebase when the reaction is performed in the presence of the base isusually 1 to 2 mole per 1 mol of the compound (6), while the base may beused in an excess amount in case that the base used is liquid under thereaction conditions such as pyridine, and the like.

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the present compound can be isolatedby pouring the reaction mixture into water, and extracting the mixturewith an organic solvent, or collecting a deposited precipitation byfiltration. The isolated present compound may be further purified byrecrystallization, chromatography, or the like.

Process B-2

Among the present compounds, a compound represented by the formula(I-iv):

wherein R¹, R², R³, R⁴, A², J, Q and n are as defined above (hereinafterreferred to as the compound (I-iv)) can be produced by reacting thecompound (6) and a compound represented by the formula (8):

wherein J is as defined above (hereinafter, referred to as the compound(8)) in the presence of a dehydrating agent.

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (8) used in the reaction is usually 1 to 2mols per 1 mol of the compound (6).

Examples of the dehydrating agent to be used in the reaction includecarbodiimides such as dicyclohexylcarbodiimide (DCC),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), andthe like. The amount of the dehydrating agent to be used is usually 1 to2 mols per 1 mol of the compound (6).

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (I-iv) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (1-iv) may be further purified byrecrystallization, chromatography, or the like.

Process C-1

Among the present compounds, a compound represented by the formula(I-v):

wherein R², R³, R⁴, J, Q and n are as defined above (hereinafter,referred to as the compound (1-v)) can be produced by reacting acompound represented by the formula (9):

wherein R⁴, J and n are as defined above (hereinafter, referred to asthe compound (9)) and a compound represented by the formula (10):

wherein R², R³ and Q are as defined above (hereinafter, referred to asthe compound (10)).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent used in the reaction include ethers such as1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidaozolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (10) to be used in the reaction is usually 1to 20 mols per 1 mol of the compound (9).

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 48 hours.

After completion of the reaction, the compound (1-v) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (1-v) may be further purified byrecrystallization, chromatography, or the like.

Process C-2

Among the present compounds, a compound represented by the formula(I-yl):

wherein R², R³, R⁴, A¹, J, Q and n are as defined above, R^(1-a)represents C1-C6 alkyl optionally substituted with at least one halogenatom; C2-C6 cyanoalkyl group; C2-C6 alkoxyalkyl optionally substitutedwith at least one halogen atom; C2-C6 alkenyl optionally substitutedwith at least one halogen atom; C3-C6 alkynyl optionally substitutedwith at least one halogen atom; or C7-C9 phenylalkyl in which a benzenering part may be substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyanogroup, (3) nitro group, (4) C1-C6 alkyl optionally substituted with atleast one halogen atom and (5) C1-C6 alkoxy optionally substituted withat least one halogen atom (hereinafter, referred to as the compound(1-yl)) can be produced by reacting a compound represented by theformula (11):

wherein R^(1-a), R⁴, A¹, J and n are as defined above, and L³ representsa halogen atom (hereinafter, referred to as the compound (11)) and thecompound (10).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichlorethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-diethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (10) to be used in the reaction is usually 1to 2 mols per 1 mol of the compound (11).

The reaction is performed in the presence of a base, if necessary.Examples of the base include nitrogen-containing heterocyclic compoundssuch as pyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene(DBN), and the like, tertiary amines such as triethylamine,N,N-diisopropylethylamine, and the like, and inorganic bases such aspotassium carbonate, sodium hydride, and the like. The amount of thebase to be used when the reaction is performed in the presence of thebase is usually 1 to 2 mols per 1 mol of the compound (11), while thebase may be used in an excess amount in the case that the base used isliquid under the reaction conditions such as pyridine and the like.

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-yl) can be isolatedafter pouring the reaction mixture into water, and extracting themixture with an organic solvent, or collecting a deposited precipitateby filtration. The isolated compound (1-yl) may be further purified byrecrystallization, chromatography or the like.

Process C-3

The compound (1-yl) can also be produced by reacting a compoundrepresented by the formula (12):

wherein R⁴, R^(1-a), A¹, J and n are as defined above (hereinafter,referred to as Compound (12)) and the compound (10) in the presence of adehydrating agent.

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichlroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (10) used in the reaction is usually 1 to 2mols per 1 mol of the compound (12).

Examples of the dehydrating agent used in the reaction includecarbodiimides such as dicyclohexylcarbodiimide (DCC),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), andthe like. The amount of the dehydrating agent to be used is usually 1 to2 mols per 1 mol of the compound (12).

The reaction temperature is usually in a range of 0 to 100° C., and thereaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-yl) can be isolated bypouring the reaction mixture into water and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (1-yl) may be further purified byrecrystallization, chromatography, or the like.

Then, a process for producing intermediates for producing the presentcompound will be explained.

Reference Process 1

Among the compound (2), a compound represented by the formula (2-i):

wherein R², R³, R⁴, J and n are as defined above (hereinafter, referredto as the compound (2-i)) can be produced by reacting the compound (9)and a compound represented by the formula (13):

wherein R² and R³ are as defined above (hereinafter, referred to as thecompound (13)).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent used in the reaction include ethers such as1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene andthe like, hydrocarbons such as toluene, benzene, xylene and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like,alcohols such as methanol, ethanol, 2-propanol, and the like, and amixture thereof.

The amount of the compound (13) to be used in the reaction is usually 1to 5 mols per 1 mol of the compound (9).

The reaction temperature is usually in a range of −50 to 100° C., andthe reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (2-i) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (2-i) may be further purified byrecrystallization, chromatography, or the like.

Reference Process 2

Among the compound (2), a compound represented by the formula (2-ii):

wherein R², R³, R⁴, J and n are as defined above (hereinafter, referredto as Compound (2-ii)) can be produced by reacting a compoundrepresented by the formula (14):

wherein R⁴, J and n are as defined above (hereinafter, referred to asthe compound (14)) and the compound (13).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like,alcohols such as methanol, ethanol, 2-propanol, and the like, and amixture thereof.

The amount of the compound (13) to be used in the reaction is usually 1to 5 mols per 1 mol of the compound (14).

The reaction temperature is usually in a range of −50 to 100° C., andthe reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (2-ii) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated compound (2-ii) may be further purified byrecrystallization, chromatography, or the like.

Reference Process 3

Among the compound (2), a compound represented by the formula (2-iii):

wherein R^(1-n), R², R³, R⁴, A¹, J and n are as defined above(hereinafter, referred to as the compound (2-iii)) can be produced byreacting the compound (11) and the compound (13).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent used in the reaction include ethers such as1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of Compound (13) used in the reaction is usually 2 to 10 molsper 1 mol of the compound (11).

The reaction temperature is usually in a range of −50 to 100° C., andthe reaction time is in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (2-iii) can be isolatedby pouring the reaction mixture into water, and extracting the mixturewith an organic solvent, or collecting a deposited precipitate byfiltration. The isolated compound (2-iii) may be further purified byrecrystallization, chromatography, or the like.

Reference Process 4

The compound (9) can be produced by reacting a compound represented bythe formula (16).

wherein R⁴ and n are as defined above (hereinafter, referred to as thecompound (16)) and a compound represented by the formula (7′):

wherein J and L² are as defined above (hereinafter, referred to asCompound (7′)).

The reaction is performed in the presence or the absence of a solvent inthe presence of a base. Examples of the solvent to be used in thereaction include ethers such as 1,4-dioxane, diethyl ether,tetrahydrofuran, methyl tert-butyl ether, and the like, halogenatedhydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such astoluene, benzene, xylene, and the like, nitriles such as acetonitrile,and the like, aprotic polar solvents such as N,N-dimethylformamide,N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide,and the like, and a mixture thereof.

The amount of the compound (7′) used in the reaction is usually 0.5 to 2mols per 1 mol of the compound (16).

Examples of the base to be used in the reaction includenitrogen-containing heterocyclic compounds such as pyridine, picoline,2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU),1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary aminessuch as triethylamine, N,N-diisopropylethylamine, and the like, andinorganic bases such as potassium carbonate, sodium hydride, and thelike. The amount of the base to be used is usually 1 to 2 mols per 1 molof the compound (16), while the base may be used in an excess amount incase that the base is liquid under the reaction conditions such aspyridine, and the like.

The reaction temperature is usually in a range of 50 to 150° C., and thereaction time is usually in a range of 1 to 24 hours.

After completion of the reaction, the compound (9) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitates byfiltration. The isolated compound (9) may be further purified byrecrystallization, chromatography, or the like.

Reference Process 5

The compound (9) can be produced by reacting a compound represented bythe formula (17):

wherein R⁴ and n are as defined above (hereinafter, referred to asCompound (17)) and the compound (7′).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The process comprises the following step 5-1 and step 5-2.

Step 5-1

This step is performed by reacting the compound (17) and the compound(7′) in the presence of a base.

The amount of the compound (7′) to be used in this step is usually 1 to2 mols per 1 mol of the compound (17). Examples of the base includenitrogen-containing heterocyclic compounds such as pyridine, picoline,2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU),1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary aminessuch as triethylamine, N,N-diisopropylethylamine, and the like, andinorganic bases such as potassium carbonate, sodium hydride, and thelike. The amount of the base to be used is usually 1 to 2 mols per 1 molof the compound (17).

The reaction temperature of this step is usually in a range of 0 to 50°C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of this step, usually, the reaction mixture is used asit is in the next step 5-2.

Step 5-2

This step is performed by reacting the reaction mixture in the step 5-1and a sulfonyl halide in the presence of a base.

Examples of the sulfonyl halide used in this step includemethanesulfonyl chloride, p-toluenesulfonyl chloride, andtrifluoromethanesulfonyl chloride. The amount of the sulfonyl halide tobe used in this step is usually 1 to 2 mols per 1 mol of the compound(17) used in the step 5-1.

Examples of the base include the same bases as those described withrespect to the step 5-1. The amount of the base is usually 2 to 4 molsper 1 mol of the compound (17) used in the step 5-1.

The reaction temperature of this step is usually in a range of 0 to 50°C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of this step, the compound (9) can be isolated bypouring the reaction mixture into water, followed by conventionalextraction with an organic solvent. The isolated compound (9) may befurther purified by recrystallization, chromatography, or the like.

Reference Process 6

The compound (14) can be produced by reacting the compound (9) with athiocarbonylation agent.

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,diglyme, and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, pyridines such as pyridine,picoline, lutidine, and the like, and a mixture thereof.

Examples of the thiocarbonylation agent to be used in the reactioninclude diphosphorus pentasulfide, a Lawesson's reagent(2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide),and the like.

The amount of the thiocarbonylation agent to be used in the reaction isusually 1 to 3 mols per 1 mol of the compound (9).

The reaction temperature is usually in a range of 0° C. to 200° C., andthe reaction time is usually in a range of 1 to 24 hours.

After completion of the reaction, the compound (14) can be isolated bycollecting a precipitate deposited in the reaction mixture byfiltration, or extracting the reaction mixture with an organic solvent.The isolated compound (14) may be further purified by recrystallization,chromatography, or the like.

Reference Process 7

The compound (11) can be produced by reacting the compound (12) with ahalogenating agent.

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

Examples of the halogenating agent to be used in the reaction includethionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorusoxybromide, phosphorus pentachloride, oxalyl chloride, and phosgene.

The amount of the halogenating agent to be used in the reaction isusually 1 to 2 mols per 1 mol of the compound (12) and, in some cases,the halogenating agent may be used in an excess amount.

The reaction temperature is usually in a range of 0° C. to 150° C., andthe reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (11) can be isolated bycollecting a precipitate deposited in the reaction mixture, orconcentrating the reaction mixture. The isolated compound (11) isusually used as it is in the next step and, if necessary, may be furtherpurified by recrystallization, or the like.

Reference Process 8

The compound (12) can be produced by reacting a compound represented bythe formula (18′):

wherein R^(1-a), R⁴ and n are as defined above (hereinafter, referred toas the compound (18′)) and the compound (7).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent used in the reaction include ethers such as1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and amixture thereof.

The amount of the compound (7) to be used in the reaction is usually 1to 2 mols per 1 mol of the compound (18′).

The reaction is performed in the presence of a base. Examples of thebase to be used include nitrogen-containing heterocyclic compounds suchas pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene(DBU), 1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiaryamines such as triethylamine, N,N-diisopropylethylamine, and the like,inorganic bases such as potassium carbonate, sodium hydride, and thelike. The amount of the base to be used is usually 1 to 2 mols per 1 molof the compound (18′).

The reaction temperature is usually in a range of 0 to 50° C., and thereaction time is usually in range of 0.1 to 24 hours.

After completion of the reaction, the compound (12) can be isolated bypouring the reaction mixture into water, followed by conventionalextraction with an organic solvent, or collecting a depositedprecipitate by filtration. The isolated compound (12) may be furtherpurified by recrystallization, chromatography, or the like.

Reference Process 9

The compound (6) can be produced by reacting a compound represented bythe formula (20):

wherein R′, R⁴ and n are as defined above (hereinafter, referred to asthe compound 20)) and the compound (10).

The reaction is performed in the presence or the absence of a solvent.Examples of the solvent used in the reaction include ethers such as1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether,and the like, halogenated hydrocarbons such as dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, andthe like, hydrocarbons such as toluene, benzene, xylene, and the like,nitriles such as acetonitrile, and the like, aprotic polar solvents suchas N,N-dimethylformamide, N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like,alcohols such as methanol, ethanol, isopropyl alcohol, and the like, anda mixture thereof.

The amount of the compound (10) to be used in the reaction is usually 1to 2 mols per 1 mol of the compound (20).

The reaction temperature is usually in a range of −20 to 150° C., andthe reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (20) can be isolated bypouring the reaction mixture into water, and extracting the mixture withan organic solvent, or collecting a deposited precipitate by filtration.The isolated Compound (20) may be further purified by recrystallization,chromatography, or the like.

The compounds (3), (4) and (13) are known compounds, or can be producedfrom known compounds according to known processes (e.g. see OrganicFunctional Group Preparations, 2nd edition, Vol. 1, chapter 12, pp.359-376 (Stanley R. Sandler, Wolf Karo.) or Organic Functional GroupPreparations, 2nd edition, Vol. 1, chapter 14, pp. 434-465 (Stanley R.Sandler, Wolf Karo.)).

As an aspect of the compound (2), the following compound is mentioned:

A hydrazide compound of the formula (II):

wherein

X^(a) represents a nitrogen atom or CR^(20ax);

Y and Z represent independently a nitrogen atom or CR^(4b), but not Yand Z are CR^(4b) at the same time;

R¹ is a hydrogen atom or C1-C6 alkyl optionally substituted with one ormore halogen atoms;

R² represent a hydrogen atom, C1-C6 alkyl optionally substituted withone or more halogen atoms, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6alkenyl optionally substituted with one or more halogen atoms, C2-C6alkynyl optionally substituted with one or more halogen atoms, C3-C6cycloalkyl optionally substituted with one or more halogen atoms, C1-C6alkylthio optionally substituted with one or more halogen atoms, C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms,C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6trialkylsilyl;

or represents phenyl, C7-C9 phenylalkyl or phenylcarbonyl: each saidphenyl ring optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl;

R^(4a), R^(4b) and R^(4c) are independently a halogen atom, cyano,nitro, hydroxyl, carboxyl, C1-C6 alkyl optionally substituted with oneor more halogen atoms, C1-C6 alkoxy optionally substituted with one ormore halogen atoms, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, C2-C6 alkenyl optionallysubstituted with one or more halogen atoms, C2-C6 alkynyl optionallysubstituted with one or more halogen atoms, C3-C6 cycloalkyl optionallysubstituted with one or more halogen atoms, C1-C6 alkylthio optionallysubstituted with one or more halogen atoms, C1-C6 alkylsulfinyloptionally substituted with one or more halogen atoms, C1-C6alkylsulfonyl optionally substituted with one or more halogen atoms,C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C3-C6 trialkylsilyl;

or represents independently phenyl, benzyl or phenoxy, each ringoptionally substituted with one or more substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4)hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with oneor more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxyoptionally substituted with one or more halogen atoms, (9) C2-C6cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one ormore halogen atoms, (11) C2-C6 alkenyl optionally substituted with oneor more halogen atoms, (12) C2-C6 alkynyl optionally substituted withone or more halogen atoms, (13) C3-C6 cycloalkyl optionally substitutedwith one or more halogen atoms, (14) C1-C6 alkylthio optionallysubstituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyloptionally substituted with one or more halogen atoms, (16) C1-C6alkylsulfonyl optionally substituted with one or more halogen atoms,(17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl,(22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24)C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl;

or 5- or 6-membered heteroaromatic optionally substituted with one ormore substituents selected from the group consisting of (1) a halogenatom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyloptionally substituted with one or more halogen atoms, (7) C1-C6hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or morehalogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, (11) C2-C6 alkenyloptionally substituted with one or more halogen atoms, (12) C2-C6alkynyl optionally substituted with one or more halogen atoms, (13)C3-C6 cycloalkyl optionally substituted with one or more halogen atoms,(14) C1-C6 alkylthio optionally substituted with one or more halogenatoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or morehalogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with oneor more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino,(19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl;

R^(19ax) represent a hydrogen atom; C1-C6 alkyl optionally substitutedwith one or more halogen atoms; C2-C6 cyanoalkyl; C2-C6 alkoxyalkyloptionally substituted with one or more halogen atoms; C2-C6 alkenyloptionally substituted with one or more halogen atoms; C2-C6 alkynyloptionally substituted with one or more halogen atoms; C3-C6 cycloalkyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, and (2) C1-C6alkyl optionally substituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms;

C7-C9 phenylalkyl whose phenyl ring is optionally substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms;

or C7-C9 pyridinylalkyl whose pyridine ring is optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms, (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; and

R^(20ax), R^(20ay) and R^(20az) represent a halogen atom; cyano; nitro;thiocyanato; C1-C6 alkyl optionally substituted with one or more halogenatoms; C1-C6 alkoxy optionally substituted with one or more halogenatoms; C2-C6 cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substitutedwith one or more halogen atoms; C2-C6 alkenyloxy optionally substitutedwith one or more halogen atoms; C2-C6 alkynyloxy optionally substitutedwith one or more halogen atoms; C1-C6 alkylthio optionally substitutedwith one or more halogen atoms; C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms; C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms; phenyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms;

or phenoxy optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms.

The compound (10) can be produced, for example, according to thefollowing scheme (1).

In Scheme (I), A³⁴, L¹, Q′, R², R³ and R^(9a) are as defined above.

Among the compound (10), a compound represented by the formula (10-i):

wherein R², R³ and R⁷ are as defined above, can be produced, forexample, according to the following scheme (2).

In Scheme (2), R², R³ and R⁷ are as defined above.

The compound (17) can be produced, for example, according to thefollowing Scheme (3).

In Scheme (3), R⁴ and n are as defined above.

The compounds (16), (18′) and (20) can be produced, for example,according to the following Scheme (4).

In Scheme (4), R^(1-a), R⁴ and n are as defined above, and L⁴ representsa leaving group (e.g. a halogen atom, a methanesulfonyloxy group, ap-toluenesulfonyloxy etc.).

The compound (8) can be produced, for example, according to the processshown in the following Scheme (7).

In Scheme (7), J is as defined above, R′⁷ represents a methyl or anethyl group, LDA represents lithium diisopropylamide, n-BuLi representsnormal butyl lithium, and t-BuLi represents tertiary butyl lithium.

Among the compound (8), a compound represented by the

wherein R^(13a), R^(14a), X^(a), Y^(a), Z^(a) and p are as definedabove, can be produced, for example, according to the process shown inthe following Scheme (8).

In Scheme (8), R^(13a), R^(14a), X^(a), Y^(a), Z^(a), p, LDA and n-BuLiare as defined above, and L⁵ represents a leaving group (e.g. a halogenatom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, amethylsulfonyl etc.).

Among the compound (8), a compound represented by the formula (8-ii):

wherein R^(14a) and p are as defined above, R^(18a), R^(18b), R^(18c)and R^(18d) each, independently, represent a hydrogen atom, a halogenatom, cyano group, nitro group, C1-C6 alkyl optionally substituted withat least one halogen atom, C1-C6 alkoxy optionally substituted with atleast one halogen atom, C1-C6 alkylthio optionally substituted with atleast one halogen atom, C1-C6 alkylsulfinyl optionally substituted withat least one halogen atom, or C1-C6 alkylsulfonyl optionally substitutedwith at least one halogen atom, can be produced, for example, accordingto the process shown in the following Scheme (9).

In Scheme (9), R^(14a), R^(18a), R^(18b), R^(18c), R^(18d), LDA and pare as defined above, and L⁶ represents a leaving group (e.g. a halogenatom, a methylsulfonyl etc.).

Among the compound (8), a compound represented by the formula (8-iii):

wherein R^(18a), R^(18b), R_(18c), R^(18d) and R^(18e) independentlyrepresent a hydrogen atom, a halogen atom, cyano group, nitro group,C1-C6 alkyl optionally substituted with at least one halogen atom, C1-C6alkoxy optionally substituted with at least one halogen atom, C1-C6alkylthio optionally substituted with at least one halogen atom, C1-C6alkylsulfinyl optionally substituted with at least one halogen atom, orC1-C6 alkylsulfonyl optionally substituted with at least one halogenatom, can be produced, for example, according to the process shown inthe following Scheme (10).

In Scheme (10), R^(18a), R^(18b), R^(18c), R^(18d) and R^(18e) are asdefined above.

Among the compound (8), a compound represented by the formula (8-iv):

wherein X¹⁸ represents —N═, or —CR^(18e)═; R^(18a), R^(18b), R^(18c),R^(18d) and R^(18e) are as defined above, and R^(14a-1) represents C1-C6alkyl optionally substituted with at least one halogen atom, can beproduced, for example, according to the process shown in the followingScheme (11).

In Scheme (11), R^(14a-1), R¹⁷, R^(18a), R^(18b), R^(18c), R^(18d) andX¹⁸ are as defined above, and R²⁰ represents a methyl or an ethyl group.

Among the compound (8), a compound represented by the formula (8-vii):

wherein R^(13b), R^(14b), X^(b), Y^(b), Z^(b) and q are as definedabove, can be produced, for example, according to the process shown inthe following Scheme (14).

In Scheme (14), R^(13b), R^(14b), R¹⁷, X^(b), Y^(b), Z^(b), L⁵ and q areas defined above.

Among the compound (8), a compound represented by the formula (8-viii)and the formula (8-ix):

[wherein

R^(13b), is as defined above;

X¹⁹ represents —N═, or —CR^(19e)═; and

R^(19a), R^(19b), R^(19c), R^(19d) and R^(19e), each, independently,represent a hydrogen atom, a halogen atom, cyano group, a nitro group,C1-C6 alkyl optionally substituted with at least one halogen atom, C1-C6alkoxy optionally substituted with at least one halogen atom, C1-C6alkylthio optionally substituted with at least one halogen atom, C1-C6alkylsulfinyl optionally substituted with at least one halogen atom, orC1-C6 alkylsulfonyl optionally substituted with at least one halogenatom]

can be produced, for example, according to the process shown in thefollowing Scheme (15).

In Scheme (15), R^(13b), R¹⁷, R^(19a), R^(19b), R^(19c), R^(19d), L⁵ andX¹⁹ are as defined above.

Among the compound (7), a compound represented by the

wherein L² and J are as defined above, can be produced, for example,according to the process shown in the following Scheme (16).

In Scheme (16), L² and J are as defined above.

Among the compound (7), a compound represented by the formula (7-ii):

wherein L² and J are as defined above, can be produced, for example,according to the process shown in the following scheme (17).

In Scheme (17), L² and J are as defined above, LDA represents lithiumdiisopropylamide, n-BuLi represents normal butyl lithium, and t-BuLirepresents tertiary butyl lithium.

Among the compound (8), a compound represented by the formula (8-v):

wherein R^(18a), R^(18b), R_(18c), R^(18d) and X¹⁸ are as defined above,and R^(14ax), R^(14ay), X^(14az) and X independently represent ahydrogen atom, a halogen atom, cyano group, C1-C6 alkyl optionallysubstituted with at least one halogen atom, C1-C6 alkoxy optionallysubstituted with at least one halogen atom, C1-C6 alkylthio optionallysubstituted with at least one halogen atom, C1-C6 alkylsulfinyloptionally substituted with at least one halogen atom, or C1-C6alkylsulfonyl optionally substituted with at least one halogen atom, canbe produced, for example, according to the process shown in thefollowing Scheme (18).

In Scheme (18) R^(18a), R^(18b), R^(18c), R^(18d), X¹⁸, R^(14ax),R^(14ay), and X^(14az) are as defined above.

The compounds (21) in scheme (18) can be produced, for example,according to the process shown in the following Scheme (19).

In Scheme (19), R^(18a), R^(18b), R^(18c), R^(18d), R^(18e), X¹⁸,R^(14ax), R^(14ay), X^(14az) and L⁶ are as defined above

Among the compounds (21) in scheme (18), a compound represented by theformula (21-i), the formula (21-ii), and the formula (21-iii):

wherein R^(18a), R^(18b), R^(18c), R^(18d) and X¹⁸ are as defined above,and halo(x) and halo(y) independently represent a halogen atom, can beproduced, for example, according to the process shown in the followingScheme (20).

In Scheme (20), R^(18a), R^(18b), R^(18c), R^(18d), X¹⁸, halo(x) andhalo(y) are as defined above.

Among the compound (8), a compound represented by the formula (8-yl):

wherein R^(18a), R^(18b), R^(18c), R^(18d) and X¹⁸ are as defined above,R^(14ay-1) represents a hydrogen atom or a halogen atom, R³⁰ representsC1-C6 alkyl optionally substituted with at least one halogen atom, and rrepresents an integer of 0 to 2, can be produced, for example, accordingto the process shown in the following Scheme (21).

In Scheme (21), R^(18a), R^(18b), R^(18c), R^(18d), X¹⁸, R^(14ay-1),R³⁰, r and L⁴ are as defined above.

The specific examples of the present compound are summarized in thefollowing compounds 1 to 277.

Compound 1:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 2:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 3:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 4:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 5:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 6:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 7:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 8:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 9:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 10:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 11:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 12:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 13:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 14:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 15:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 16:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 17:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 18:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 19:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 20:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 21:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 22:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 23:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 24:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 25:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 26:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 27:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 28:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 29:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 30:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 31:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 32:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 33:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 34:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 35:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 36:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 37:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 38:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 39:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 40:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 41:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 42:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 43:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 44:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 45:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 46:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 47:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 48:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 49:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 50:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 51:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 52:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 53:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 54:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 55:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 56:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 57:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 58:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 59:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 60:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 61:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 62:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 63:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

Compound 64:

Compounds of formula 1A wherein R², R³, M, R^(19a), R^(20ay) and Xcorresponds to a row in Table A, and E substituted with (R⁴)_(n) is:

TABLE A No. R² R³ M R^(19a) X R^(20ay) H H H 3-chloro-2- N Cl pyridinylMe H H 3-chloro-2- N Cl pyridinyl H Me H 3-chloro-2- N Cl pyridinyl MeMe H 3-chloro-2- N Cl pyridinyl Et H H 3-chloro-2- N Cl pyridinyl H Et H3-chloro-2- N Cl pyridinyl Et Et H 3-chloro-2- N Cl pyridinyl n-Pr H H3-chloro-2- N Cl pyridinyl H n-Pr H 3-chloro-2- N Cl pyridinyl iso-Pr HH 3-chloro-2- N Cl pyridinyl H iso-Pr H 3-chloro-2- N Cl pyridinyliso-Bu H H 3-chloro-2- N Cl pyridinyl H iso-Bu H 3-chloro-2- N Clpyridinyl tert-Bu H H 3-chloro-2- N Cl pyridinyl H tert-Bu H 3-chloro-2-N Cl pyridinyl CH₂CF₃ H H 3-chloro-2- N Cl pyridinyl H CH₂CF₃ H3-chloro-2- N Cl pyridinyl CH₂CN H H 3-chloro-2- N Cl pyridinyl H CH₂CNH 3-chloro-2- N Cl pyridinyl CH₂OMe H H 3-chloro-2- N Cl pyridinyl HCH₂OMe H 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ H H 3-chloro-2- N Clpyridinyl H CH₂CH═CH₂ H 3-chloro-2- N Cl pyridinyl CH₂CCH H H3-chloro-2- N Cl pyridinyl H CH₂CCH H 3-chloro-2- N Cl pyridinyl H CO₂MeH 3-chloro-2- N Cl pyridinyl Me Et H 3-chloro-2- N Cl pyridinyl Et Me H3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ Me H 3-chloro-2- N Cl pyridinylCH₂CH═CH₂ Et H 3-chloro-2- N Cl pyridinyl Me CH₂CH═CH₂ H 3-chloro-2- NCl pyridinyl Et CH₂CH═CH₂ H 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂CH₂CH═CH₂ H 3-chloro-2- N Cl pyridinyl CH₂CCH Me H 3-chloro-2- N Clpyridinyl CH₂CCH Et H 3-chloro-2- N Cl pyridinyl Me CH₂CCH H 3-chloro-2-N Cl pyridinyl Et CH₂CCH H 3-chloro-2- N Cl pyridinyl CH₂CCH CH₂CCH H3-chloro-2- N Cl pyridinyl cyc-Pr H H 3-chloro-2- N Cl pyridinyl Hcyc-Pr H 3-chloro-2- N Cl pyridinyl iso-Bu iso-Bu H 3-chloro-2- N Clpyridinyl sec-Bu H H 3-chloro-2- N Cl pyridinyl H sec-Bu H 3-chloro-2- NCl pyridinyl cyc-Bu H H 3-chloro-2- N Cl pyridinyl H cyc-Bu H3-chloro-2- N Cl pyridinyl CH₂₋cyc-Pr H H 3-chloro-2- N Cl pyridinyl HCH₂₋cyc-Pr H 3-chloro-2- N Cl pyridinyl CH₂₋cyc-Bu H H 3-chloro-2- N Clpyridinyl H CH₂₋cyc-Bu H 3-chloro-2- N Cl pyridinyl CH₂CF₃ Me H3-chloro-2- N Cl pyridinyl CH₂CF₃ Et H 3-chloro-2- N Cl pyridinyl MeCH₂CF₃ H 3-chloro-2- N Cl pyridinyl Et CH₂CF₃ H 3-chloro-2- N Clpyridinyl CH₂CF₃ CH₂CF₃ H 3-chloro-2- N Cl pyridinyl CH₂CN Me H3-chloro-2- N Cl pyridinyl CH₂CN Et H 3-chloro-2- N Cl pyridinyl MeCH₂CN H 3-chloro-2- N Cl pyridinyl Et CH₂CN H 3-chloro-2- N Cl pyridinylCH₂CN CH₂CN H 3-chloro-2- N Cl pyridinyl CH₂CH₂OMe H H 3-chloro-2- N Clpyridinyl H CH₂CH₂OMe H 3-chloro-2- N Cl pyridinyl CH₂CH₂OMe CH₂CH₂OMe H3-chloro-2- N Cl pyridinyl CH₂CH₂SMe H H 3-chloro-2- N Cl pyridinyl HCH₂CH₂SMe H 3-chloro-2- N Cl pyridinyl Me CO₂Me H 3-chloro-2- N Clpyridinyl Et CO₂Me H 3-chloro-2- N Cl pyridinyl H 2- H 3-chloro-2- N Clpyridinyl pyridinyl H 3- H 3-chloro-2- N Cl pyridinyl pyridinyl H 4- H3-chloro-2- N Cl pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- N Clpyridinyl —(CH₂)₄— H 3-chloro-2- N Cl pyridinyl —CH₂NHCH₂— H 3-chloro-2-N Cl pyridinyl —CH₂NMeCH₂— H 3-chloro-2- N Cl pyridinyl—CH₂N(iso-Pr)CH₂— H 3-chloro-2- N Cl pyridinyl —CH₂N(CHO)CH₂— H3-chloro-2- N Cl pyridinyl —CH₂N(Ac)CH₂— H 3-chloro-2- N Cl pyridinyl—CH₂N(CO₂Me)CH₂— H 3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Et)CH₂— H3-chloro-2- N Cl pyridinyl H H H 3-chloro-2- N Br pyridinyl Me H H3-chloro-2- N Br pyridinyl H Me H 3-chloro-2- N Br pyridinyl Me Me H3-chloro-2- N Br pyridinyl Et H H 3-chloro-2- N Br pyridinyl H Et H3-chloro-2- N Br pyridinyl Et Et H 3-chloro-2- N Br pyridinyl n-Pr H H3-chloro-2- N Br pyridinyl H n-Pr H 3-chloro-2- N Br pyridinyl iso-Pr HH 3-chloro-2- N Br pyridinyl H iso-Pr H 3-chloro-2- N Br pyridinyliso-Bu H H 3-chloro-2- N Br pyridinyl H iso-Bu H 3-chloro-2- N Brpyridinyl tert-Bu H H 3-chloro-2- N Br pyridinyl H tert-Bu H 3-chloro-2-N Br pyridinyl CH₂CF₃ H H 3-chloro-2- N Br pyridinyl H CH₂CF₃ H3-chloro-2- N Br pyridinyl CH₂CN H H 3-chloro-2- N Br pyridinyl H CH₂CNH 3-chloro-2- N Br pyridinyl CH₂OMe H H 3-chloro-2- N Br pyridinyl HCH₂OMe H 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ H H 3-chloro-2- N Brpyridinyl H CH₂CH═CH₂ H 3-chloro-2- N Br pyridinyl CH₂CCH H H3-chloro-2- N Br pyridinyl H CH₂CCH H 3-chloro-2- N Br pyridinyl H CO₂MeH 3-chloro-2- N Br pyridinyl Me Et H 3-chloro-2- N Br pyridinyl Et Me H3-chloro-2- N Br pyridinyl CH₂CH═CH₂ Me H 3-chloro-2- N Br pyridinylCH₂CH═CH₂ Et H 3-chloro-2- N Br pyridinyl Me CH₂CH═CH₂ H 3-chloro-2- NBr pyridinyl Et CH₂CH═CH₂ H 3-chloro-2- N Br pyridinyl CH₂CH═CH₂CH₂CH═CH₂ H 3-chloro-2- N Br pyridinyl CH₂CCH Me H 3-chloro-2- N Brpyridinyl CH₂CCH Et H 3-chloro-2- N Br pyridinyl Me CH₂CCH H 3-chloro-2-N Br pyridinyl Et CH₂CCH H 3-chloro-2- N Br pyridinyl CH₂CCH CH₂CCH H3-chloro-2- N Br pyridinyl cyc-Pr H H 3-chloro-2- N Br pyridinyl Hcyc-Pr H 3-chloro-2- N Br pyridinyl iso-Bu iso-Bu H 3-chloro-2- N Brpyridinyl sec-Bu H H 3-chloro-2- N Br pyridinyl H sec-Bu H 3-chloro-2- NBr pyridinyl cyc-Bu H H 3-chloro-2- N Br pyridinyl H cyc-Bu H3-chloro-2- N Br pyridinyl CH₂₋cyc-Pr H H 3-chloro-2- N Br pyridinyl HCH₂₋cyc-Pr H 3-chloro-2- N Br pyridinyl CH₂₋cyc-Bu H H 3-chloro-2- N Brpyridinyl H CH₂₋cyc-Bu H 3-chloro-2- N Br pyridinyl CH₂CF₃ Me H3-chloro-2- N Br pyridinyl CH₂CF₃ Et H 3-chloro-2- N Br pyridinyl MeCH₂CF₃ H 3-chloro-2- N Br pyridinyl Et CH₂CF₃ H 3-chloro-2- N Brpyridinyl CH₂CF₃ CH₂CF₃ H 3-chloro-2- N Br pyridinyl CH₂CN Me H3-chloro-2- N Br pyridinyl CH₂CN Et H 3-chloro-2- N Br pyridinyl MeCH₂CN H 3-chloro-2- N Br pyridinyl Et CH₂CN H 3-chloro-2- N Br pyridinylCH₂CN CH₂CN H 3-chloro-2- N Br pyridinyl CH₂CH₂OMe H H 3-chloro-2- N Brpyridinyl H CH₂CH₂OMe H 3-chloro-2- N Br pyridinyl CH₂CH₂OMe CH₂CH₂OMe H3-chloro-2- N Br pyridinyl CH₂CH₂SMe H H 3-chloro-2- N Br pyridinyl HCH₂CH₂SMe H 3-chloro-2- N Br pyridinyl Me CO₂Me H 3-chloro-2- N Brpyridinyl Et CO₂Me H 3-chloro-2- N Br pyridinyl H 2- H 3-chloro-2- N Brpyridinyl pyridinyl H 3- H 3-chloro-2- N Br pyridinyl pyridinyl H 4- H3-chloro-2- N Br pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- N Brpyridinyl —(CH₂)₄— H 3-chloro-2- N Br pyridinyl —CH₂NHCH₂— H 3-chloro-2-N Br pyridinyl —CH₂NMeCH₂— H 3-chloro-2- N Br pyridinyl—CH₂N(iso-Pr)CH₂— H 3-chloro-2- N Br pyridinyl —CH₂N(CHO)CH₂— H3-chloro-2- N Br pyridinyl —CH₂N(Ac)CH₂— H 3-chloro-2- N Br pyridinyl—CH₂N(CO₂Me)CH₂— H 3-chloro-2- N Br pyridinyl —CH₂N(CO₂Et)CH₂— H3-chloro-2- N Br pyridinyl H H H 3-chloro-2- N CF₃ pyridinyl Me H H3-chloro-2- N CF₃ pyridinyl H Me H 3-chloro-2- N CF₃ pyridinyl Me Me H3-chloro-2- N CF₃ pyridinyl Et H H 3-chloro-2- N CF₃ pyridinyl H Et H3-chloro-2- N CF₃ pyridinyl Et Et H 3-chloro-2- N CF₃ pyridinyl n-Pr H H3-chloro-2- N CF₃ pyridinyl H n-Pr H 3-chloro-2- N CF₃ pyridinyl iso-PrH H 3-chloro-2- N CF₃ pyridinyl H iso-Pr H 3-chloro-2- N CF₃ pyridinyliso-Bu H H 3-chloro-2- N CF₃ pyridinyl H iso-Bu H 3-chloro-2- N CF₃pyridinyl tert-Bu H H 3-chloro-2- N CF₃ pyridinyl H tert-Bu H3-chloro-2- N CF₃ pyridinyl CH₂CF₃ H H 3-chloro-2- N CF₃ pyridinyl HCH₂CF₃ H 3-chloro-2- N CF₃ pyridinyl CH₂CCH CH₂CCH Me 3-chloro-2- N CF₃pyridinyl cyc-Pr H Me 3-chloro-2- N CF₃ pyridinyl H cyc-Pr Me3-chloro-2- N CF₃ pyridinyl iso-Bu iso-Bu Me 3-chloro-2- N CF₃ pyridinylsec-Bu H Me 3-chloro-2- N CF₃ pyridinyl H sec-Bu Me 3-chloro-2- N CF₃pyridinyl cyc-Bu H Me 3-chloro-2- N CF₃ pyridinyl H cyc-Bu Me3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Pr H Me 3-chloro-2- N CF₃ pyridinylH CH₂₋cyc-Pr Me 3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Bu H Me 3-chloro-2-N CF₃ pyridinyl H CH₂₋cyc-Bu Me 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Me Me3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Et Me 3-chloro-2- N CF₃ pyridinyl MeCH₂CF₃ Me 3-chloro-2- N CF₃ pyridinyl Et CH₂CF₃ Me 3-chloro-2- N CF₃pyridinyl CH₂CF₃ CH₂CF₃ Me 3-chloro-2- N CF₃ pyridinyl CH₂CN Me Me3-chloro-2- N CF₃ pyridinyl CH₂CN Et Me 3-chloro-2- N CF₃ pyridinyl MeCH₂CN Me 3-chloro-2- N CF₃ pyridinyl Et CH₂CN Me 3-chloro-2- N CF₃pyridinyl CH₂CN CH₂CN Me 3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe H Me3-chloro-2- N CF₃ pyridinyl H CH₂CH₂OMe Me 3-chloro-2- N CF₃ pyridinylCH₂CH₂OMe CH₂CH₂OMe Me 3-chloro-2- N CF₃ pyridinyl CH₂CH₂SMe H Me3-chloro-2- N CF₃ pyridinyl H CH₂CH₂SMe Me 3-chloro-2- N CF₃ pyridinylMe CO₂Me Me 3-chloro-2- N CF₃ pyridinyl Et CO₂Me Me 3-chloro-2- N CF₃pyridinyl H 2- Me 3-chloro-2- N CF₃ pyridinyl pyridinyl H 3- Me3-chloro-2- N CF₃ pyridinyl pyridinyl H 4- Me 3-chloro-2- N CF₃pyridinyl pyridinyl —(CH₂)₃— Me 3-chloro-2- N CF₃ pyridinyl —(CH₂)₄— Me3-chloro-2- N CF₃ pyridinyl —CH₂NHCH₂— Me 3-chloro-2- N CF₃ pyridinyl—CH₂NMeCH₂— Me 3-chloro-2- N CF₃ pyridinyl —CH₂N(iso-Pr)CH₂— Me3-chloro-2- N CF₃ pyridinyl —CH₂N(CHO)CH₂— Me 3-chloro-2- N CF₃pyridinyl —CH₂N(Ac)CH₂— Me 3-chloro-2- N CF₃ pyridinyl —CH₂N(CO₂Me)CH₂—Me 3-chloro-2- N CF₃ pyridinyl —CH₂N(CO₂Et)CH₂— Me 3-chloro-2- N CF₃pyridinyl H H OMe 3-chloro-2- N Cl pyridinyl Me H OMe 3-chloro-2- N Clpyridinyl H Me OMe 3-chloro-2- N Cl pyridinyl Me Me OMe 3-chloro-2- N Clpyridinyl Et H OMe 3-chloro-2- N Cl pyridinyl H Et OMe 3-chloro-2- N Clpyridinyl Et Et OMe 3-chloro-2- N Cl pyridinyl n-Pr H OMe 3-chloro-2- NCl pyridinyl H n-Pr OMe 3-chloro-2- N Cl pyridinyl iso-Pr H OMe3-chloro-2- N Cl pyridinyl H iso-Pr OMe 3-chloro-2- N Cl pyridinyliso-Bu H OMe 3-chloro-2- N Cl pyridinyl H iso-Bu OMe 3-chloro-2- N Clpyridinyl tert-Bu H OMe 3-chloro-2- N Cl pyridinyl H tert-Bu OMe3-chloro-2- N Cl pyridinyl CH₂CF₃ H OMe 3-chloro-2- N Cl pyridinyl HCH₂CF₃ OMe 3-chloro-2- N Cl pyridinyl CH₂CN H OMe 3-chloro-2- N Clpyridinyl H CH₂CN OMe 3-chloro-2- N Cl pyridinyl CH₂OMe H OMe3-chloro-2- N Cl pyridinyl H CH₂OMe OMe 3-chloro-2- N Cl pyridinylCH₂CH═CH₂ H OMe 3-chloro-2- N Cl pyridinyl H CH₂CH═CH₂ OMe 3-chloro-2- NCl pyridinyl CH₂CCH H OMe 3-chloro-2- N Cl pyridinyl H CH₂CCH OMe3-chloro-2- N Cl pyridinyl H CO₂Me OMe 3-chloro-2- N Cl pyridinyl Me EtOMe 3-chloro-2- N Cl pyridinyl Et Me OMe 3-chloro-2- N Cl pyridinylCH₂CH═CH₂ Me OMe 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ Et OMe 3-chloro-2-N Cl pyridinyl Me CH₂CH═CH₂ OMe 3-chloro-2- N Cl pyridinyl Et CH₂CH═CH₂OMe 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ CH₂CH═CH₂ OMe 3-chloro-2- N Clpyridinyl CH₂CCH Me OMe 3-chloro-2- N Cl pyridinyl CH₂CCH Et OMe3-chloro-2- N Cl pyridinyl Me CH₂CCH OMe 3-chloro-2- N Cl pyridinyl EtCH₂CCH OMe 3-chloro-2- N Cl pyridinyl CH₂CCH CH₂CCH OMe 3-chloro-2- N Clpyridinyl cyc-Pr H OMe 3-chloro-2- N Cl pyridinyl H cyc-Pr OMe3-chloro-2- N Cl pyridinyl iso-Bu iso-Bu OMe 3-chloro-2- N Cl pyridinylsec-Bu H OMe 3-chloro-2- N Cl pyridinyl H sec-Bu OMe 3-chloro-2- N Clpyridinyl cyc-Bu H OMe 3-chloro-2- N Cl pyridinyl H cyc-Bu OMe3-chloro-2- N Cl pyridinyl CH₂₋cyc-Pr H OMe 3-chloro-2- N Cl pyridinyl HCH₂₋cyc-Pr OMe 3-chloro-2- N Cl pyridinyl CH₂₋cyc-Bu H OMe 3-chloro-2- NCl pyridinyl H CH₂₋cyc-Bu OMe 3-chloro-2- N Cl pyridinyl CH₂CF₃ Me OMe3-chloro-2- N Cl pyridinyl CH₂CF₃ Et OMe 3-chloro-2- N Cl pyridinyl MeCH₂CF₃ OMe 3-chloro-2- N Cl pyridinyl Et CH₂CF₃ OMe 3-chloro-2- N Clpyridinyl CH₂CF₃ CH₂CF₃ OMe 3-chloro-2- N Cl pyridinyl CH₂CN Me OMe3-chloro-2- N Cl pyridinyl CH₂CN Et OMe 3-chloro-2- N Cl pyridinyl MeCH₂CN OMe 3-chloro-2- N Cl pyridinyl Et CH₂CN OMe 3-chloro-2- N Clpyridinyl CH₂CN CH₂CN OMe 3-chloro-2- N Cl pyridinyl CH₂CH₂OMe H OMe3-chloro-2- N Cl pyridinyl H CH₂CH₂OMe OMe 3-chloro-2- N Cl pyridinylCH₂CH₂OMe CH₂CH₂OMe OMe 3-chloro-2- N Cl pyridinyl CH₂CH₂SMe H OMe3-chloro-2- N Cl pyridinyl H CH₂CH₂SMe OMe 3-chloro-2- N Cl pyridinyl MeCO₂Me OMe 3-chloro-2- N Cl pyridinyl Et CO₂Me OMe 3-chloro-2- N Clpyridinyl H 2- OMe 3-chloro-2- N Cl pyridinyl pyridinyl H 3- OMe3-chloro-2- N Cl pyridinyl pyridinyl H 4- OMe 3-chloro-2- N Cl pyridinylpyridinyl —(CH₂)₃— OMe 3-chloro-2- N Cl pyridinyl —(CH₂)₄— OMe3-chloro-2- N Cl pyridinyl —CH₂NHCH₂— OMe 3-chloro-2- N Cl pyridinyl—CH₂NMeCH₂— OMe 3-chloro-2- N Cl pyridinyl —CH₂N(iso-Pr)CH₂— OMe3-chloro-2- N Cl pyridinyl —CH₂N(CHO)CH₂— OMe 3-chloro-2- N Cl pyridinyl—CH₂N(Ac)CH₂— OMe 3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Me)CH₂— OMe3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Et)CH₂— OMe 3-chloro-2- N Clpyridinyl H H OMe 3-chloro-2- N Br pyridinyl Me H OMe 3-chloro-2- N Brpyridinyl H Me OMe 3-chloro-2- N Br pyridinyl Me Me OMe 3-chloro-2- N Brpyridinyl Et H OMe 3-chloro-2- N Br pyridinyl H Et OMe 3-chloro-2- N Brpyridinyl Et Et OMe 3-chloro-2- N Br pyridinyl n-Pr H OMe 3-chloro-2- NBr pyridinyl H n-Pr OMe 3-chloro-2- N Br pyridinyl iso-Pr H OMe3-chloro-2- N Br pyridinyl H iso-Pr OMe 3-chloro-2- N Br pyridinyliso-Bu H OMe 3-chloro-2- N Br pyridinyl H iso-Bu OMe 3-chloro-2- N Brpyridinyl tert-Bu H OMe 3-chloro-2- N Br pyridinyl H tert-Bu OMe3-chloro-2- N Br pyridinyl CH₂CF₃ H OMe 3-chloro-2- N Br pyridinyl HCH₂CF₃ OMe 3-chloro-2- N Br pyridinyl CH₂CN H OMe 3-chloro-2- N Brpyridinyl H CH₂CN OMe 3-chloro-2- N Br pyridinyl CH₂OMe H OMe3-chloro-2- N Br pyridinyl H CH₂OMe OMe 3-chloro-2- N Br pyridinylCH₂CH═CH₂ H OMe 3-chloro-2- N Br pyridinyl H CH₂CH═CH₂ OMe 3-chloro-2- NBr pyridinyl CH₂CCH H OMe 3-chloro-2- N Br pyridinyl H CH₂CCH OMe3-chloro-2- N Br pyridinyl H CO₂Me OMe 3-chloro-2- N Br pyridinyl Me EtOMe 3-chloro-2- N Br pyridinyl Et Me OMe 3-chloro-2- N Br pyridinylCH₂CH═CH₂ Me OMe 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ Et OMe 3-chloro-2-N Br pyridinyl Me CH₂CH═CH₂ OMe 3-chloro-2- N Br pyridinyl Et CH₂CH═CH₂OMe 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ CH₂CH═CH₂ OMe 3-chloro-2- N Brpyridinyl CH₂CCH Me OMe 3-chloro-2- N Br pyridinyl CH₂CCH Et OMe3-chloro-2- N Br pyridinyl Me CH₂CCH OMe 3-chloro-2- N Br pyridinyl EtCH₂CCH OMe 3-chloro-2- N Br pyridinyl CH₂CCH CH₂CCH OMe 3-chloro-2- N Brpyridinyl cyc-Pr H OMe 3-chloro-2- N Br pyridinyl H cyc-Pr OMe3-chloro-2- N Br pyridinyl iso-Bu iso-Bu OMe 3-chloro-2- N Br pyridinylsec-Bu H OMe 3-chloro-2- N Br pyridinyl H sec-Bu OMe 3-chloro-2- N Brpyridinyl cyc-Bu H OMe 3-chloro-2- N Br pyridinyl H cyc-Bu OMe3-chloro-2- N Br pyridinyl CH₂₋cyc-Pr H OMe 3-chloro-2- N Br pyridinyl HCH₂₋cyc-Pr OMe 3-chloro-2- N Br pyridinyl CH₂₋cyc-Bu H OMe 3-chloro-2- NBr pyridinyl H CH₂₋cyc-Bu OMe 3-chloro-2- N Br pyridinyl CH₂CF₃ Me OMe3-chloro-2- N Br pyridinyl CH₂CF₃ Et OMe 3-chloro-2- N Br pyridinyl MeCH₂CF₃ OMe 3-chloro-2- N Br pyridinyl Et CH₂CF₃ OMe 3-chloro-2- N Brpyridinyl CH₂CF₃ CH₂CF₃ OMe 3-chloro-2- N Br pyridinyl CH₂CN Me OMe3-chloro-2- N Br pyridinyl CH₂CN Et OMe 3-chloro-2- N Br pyridinyl MeCH₂CN OMe 3-chloro-2- N Br pyridinyl Et CH₂CN OMe 3-chloro-2- N Brpyridinyl CH₂CN CH₂CN OMe 3-chloro-2- N Br pyridinyl CH₂CH₂OMe H OMe3-chloro-2- N Br pyridinyl H CH₂CH₂OMe OMe 3-chloro-2- N Br pyridinylCH₂CH₂OMe CH₂CH₂OMe OMe 3-chloro-2- N Br pyridinyl CH₂CH₂SMe H OMe3-chloro-2- N Br pyridinyl H CH₂CH₂SMe OMe 3-chloro-2- N Br pyridinyl MeCO₂Me OMe 3-chloro-2- N Br pyridinyl Et CO₂Me OMe 3-chloro-2- N Brpyridinyl H 2- OMe 3-chloro-2- N Br pyridinyl pyridinyl H 3- OMe3-chloro-2- N Br pyridinyl pyridinyl H 4- OMe 3-chloro-2- N Br pyridinylpyridinyl —(CH₂)₃— OMe 3-chloro-2- N Br pyridinyl —(CH₂)₄— OMe3-chloro-2- N Br pyridinyl —CH₂NHCH₂— OMe 3-chloro-2- N Br pyridinyl—CH₂NMeCH₂— OMe 3-chloro-2- N Br pyridinyl —CH₂N(iso-Pr)CH₂— OMe3-chloro-2- N Br pyridinyl —CH₂N(CHO)CH₂— OMe 3-chloro-2- N Br pyridinyl—CH₂N(Ac)CH₂— OMe 3-chloro-2- N Br pyridinyl —CH₂N(CO₂Me)CH₂— OMe3-chloro-2- N Br pyridinyl —CH₂N(CO₂Et)CH₂— OMe 3-chloro-2- N Brpyridinyl H H OMe 3-chloro-2- N CF₃ pyridinyl Me H OMe 3-chloro-2- N CF₃pyridinyl H Me OMe 3-chloro-2- N CF₃ pyridinyl Me Me OMe 3-chloro-2- NCF₃ pyridinyl Et H OMe 3-chloro-2- N CF₃ pyridinyl H Et OMe 3-chloro-2-N CF₃ pyridinyl Et Et OMe 3-chloro-2- N CF₃ pyridinyl n-Pr H OMe3-chloro-2- N CF₃ pyridinyl H n-Pr OMe 3-chloro-2- N CF₃ pyridinyliso-Pr H OMe 3-chloro-2- N CF₃ pyridinyl H iso-Pr OMe 3-chloro-2- N CF₃pyridinyl iso-Bu H OMe 3-chloro-2- N CF₃ pyridinyl H iso-Bu OMe3-chloro-2- N CF₃ pyridinyl tert-Bu H OMe 3-chloro-2- N CF₃ pyridinyl Htert-Bu OMe 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ H OMe 3-chloro-2- N CF₃pyridinyl H CH₂CF₃ OMe 3-chloro-2- N CF₃ pyridinyl CH₂CN H OMe3-chloro-2- N CF₃ pyridinyl H CH₂CN OMe 3-chloro-2- N CF₃ pyridinylCH₂OMe H OMe 3-chloro-2- N CF₃ pyridinyl H CH₂OMe OMe 3-chloro-2- N CF₃pyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- N CF₃ pyridinyl H CH₂CH═CH₂ OMe3-chloro-2- N CF₃ pyridinyl CH₂CCH H OMe 3-chloro-2- N CF₃ pyridinyl HCH₂CCH OMe 3-chloro-2- N CF₃ pyridinyl H CO₂Me OMe 3-chloro-2- N CF₃pyridinyl Me Et OMe 3-chloro-2- N CF₃ pyridinyl Et Me OMe 3-chloro-2- NCF₃ pyridinyl CH₂CH═CH₂ Me OMe 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂ EtOMe 3-chloro-2- N CF₃ pyridinyl Me CH₂CH═CH₂ OMe 3-chloro-2- N CF₃pyridinyl Et CH₂CH═CH₂ OMe 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂CH₂CH═CH₂ OMe 3-chloro-2- N CF₃ pyridinyl CH₂CCH Me OMe 3-chloro-2- NCF₃ pyridinyl CH₂CCH Et OMe 3-chloro-2- N CF₃ pyridinyl Me CH₂CCH OMe3-chloro-2- N CF₃ pyridinyl Et CH₂CCH OMe 3-chloro-2- N CF₃ pyridinylCH₂CCH CH₂CCH OMe 3-chloro-2- N CF₃ pyridinyl cyc-Pr H OMe 3-chloro-2- NCF₃ pyridinyl H cyc-Pr OMe 3-chloro-2- N CF₃ pyridinyl iso-Bu iso-Bu OMe3-chloro-2- N CF₃ pyridinyl sec-Bu H OMe 3-chloro-2- N CF₃ pyridinyl Hsec-Bu OMe 3-chloro-2- N CF₃ pyridinyl cyc-Bu H OMe 3-chloro-2- N CF₃pyridinyl H cyc-Bu OMe 3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Pr H OMe3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Pr OMe 3-chloro-2- N CF₃ pyridinylCH₂₋cyc-Bu H OMe 3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Bu OMe3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Me OMe 3-chloro-2- N CF₃ pyridinylCH₂CF₃ Et OMe 3-chloro-2- N CF₃ pyridinyl Me CH₂CF₃ OMe 3-chloro-2- NCF₃ pyridinyl Et CH₂CF₃ OMe 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ CH₂CF₃OMe 3-chloro-2- N CF₃ pyridinyl CH₂CN Me OMe 3-chloro-2- N CF₃ pyridinylCH₂CN Et OMe 3-chloro-2- N CF₃ pyridinyl Me CH₂CN OMe 3-chloro-2- N CF₃pyridinyl Et CH₂CN OMe 3-chloro-2- N CF₃ pyridinyl CH₂CN CH₂CN OMe3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe H OMe 3-chloro-2- N CF₃ pyridinylH CH₂CH₂OMe OMe 3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe CH₂CH₂OMe OMe3-chloro-2- N CF₃ pyridinyl CH₂CH₂SMe H OMe 3-chloro-2- N CF₃ pyridinylH CH₂CH₂SMe OMe 3-chloro-2- N CF₃ pyridinyl Me CO₂Me OMe 3-chloro-2- NCF₃ pyridinyl Et CO₂Me OMe 3-chloro-2- N CF₃ pyridinyl H 2- OMe3-chloro-2- N CF₃ pyridinyl pyridinyl H 3- OMe 3-chloro-2- N CF₃pyridinyl pyridinyl H 4- OMe 3-chloro-2- N CF₃ pyridinyl pyridinyl—(CH₂)₃— OMe 3-chloro-2- N CF₃ pyridinyl —(CH₂)₄— OMe 3-chloro-2- N CF₃pyridinyl —CH₂NHCH₂— OMe 3-chloro-2- N CF₃ pyridinyl —CH₂NMeCH₂— OMe3-chloro-2- N CF₃ pyridinyl —CH₂N(iso-Pr)CH₂— OMe 3-chloro-2- N CF₃pyridinyl —CH₂N(CHO)CH₂— OMe 3-chloro-2- N CF₃ pyridinyl —CH₂N(Ac)CH₂—OMe 3-chloro-2- N CF₃ pyridinyl —CH₂N(CO₂Me)CH₂— OMe 3-chloro-2- N CF₃pyridinyl —CH₂N(CO₂Et)CH₂— OMe 3-chloro-2- N CF₃ pyridinyl H H OEt3-chloro-2- N Cl pyridinyl Me H OEt 3-chloro-2- N Cl pyridinyl H Me OEt3-chloro-2- N Cl pyridinyl Me Me OEt 3-chloro-2- N Cl pyridinyl Et H OEt3-chloro-2- N Cl pyridinyl H Et OEt 3-chloro-2- N Cl pyridinyl Et Et OEt3-chloro-2- N Cl pyridinyl n-Pr H OEt 3-chloro-2- N Cl pyridinyl H n-PrOEt 3-chloro-2- N Cl pyridinyl iso-Pr H OEt 3-chloro-2- N Cl pyridinyl Hiso-Pr OEt 3-chloro-2- N Cl pyridinyl iso-Bu H OEt 3-chloro-2- N Clpyridinyl H iso-Bu OEt 3-chloro-2- N Cl pyridinyl tert-Bu H OEt3-chloro-2- N Cl pyridinyl H tert-Bu OEt 3-chloro-2- N Cl pyridinylCH₂CF₃ H OEt 3-chloro-2- N Cl pyridinyl H CH₂CF₃ OEt 3-chloro-2- N Clpyridinyl CH₂CN H OEt 3-chloro-2- N Cl pyridinyl H CH₂CN OEt 3-chloro-2-N Cl pyridinyl CH₂OMe H OEt 3-chloro-2- N Cl pyridinyl H CH₂OMe OEt3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ H OEt 3-chloro-2- N Cl pyridinyl HCH₂CH═CH₂ OEt 3-chloro-2- N Cl pyridinyl CH₂CCH H OEt 3-chloro-2- N Clpyridinyl H CH₂CCH OEt 3-chloro-2- N Cl pyridinyl H CO₂Me OEt3-chloro-2- N Cl pyridinyl Me Et OEt 3-chloro-2- N Cl pyridinyl Et MeOEt 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ Me OEt 3-chloro-2- N Clpyridinyl CH₂CH═CH₂ Et OEt 3-chloro-2- N Cl pyridinyl Me CH₂CH═CH₂ OEt3-chloro-2- N Cl pyridinyl Et CH₂CH═CH₂ OEt 3-chloro-2- N Cl pyridinylCH₂CH═CH₂ CH₂CH═CH₂ OEt 3-chloro-2- N Cl pyridinyl CH₂CCH Me OEt3-chloro-2- N Cl pyridinyl CH₂CCH Et OEt 3-chloro-2- N Cl pyridinyl MeCH₂CCH OEt 3-chloro-2- N Cl pyridinyl Et CH₂CCH OEt 3-chloro-2- N Clpyridinyl CH₂CCH CH₂CCH OEt 3-chloro-2- N Cl pyridinyl cyc-Pr H OEt3-chloro-2- N Cl pyridinyl H cyc-Pr OEt 3-chloro-2- N Cl pyridinyliso-Bu iso-Bu OEt 3-chloro-2- N Cl pyridinyl sec-Bu H OEt 3-chloro-2- NCl pyridinyl H sec-Bu OEt 3-chloro-2- N Cl pyridinyl cyc-Bu H OEt3-chloro-2- N Cl pyridinyl H cyc-Bu OEt 3-chloro-2- N Cl pyridinylCH₂₋cyc-Pr H OEt 3-chloro-2- N Cl pyridinyl H CH₂₋cyc-Pr OEt 3-chloro-2-N Cl pyridinyl CH₂₋cyc-Bu H OEt 3-chloro-2- N Cl pyridinyl H CH₂₋cyc-BuOEt 3-chloro-2- N Cl pyridinyl CH₂CF₃ Me OEt 3-chloro-2- N Cl pyridinylCH₂CF₃ Et OEt 3-chloro-2- N Cl pyridinyl Me CH₂CF₃ OEt 3-chloro-2- N Clpyridinyl Et CH₂CF₃ OEt 3-chloro-2- N Cl pyridinyl CH₂CF₃ CH₂CF₃ OEt3-chloro-2- N Cl pyridinyl CH₂CN Me OEt 3-chloro-2- N Cl pyridinyl CH₂CNEt OEt 3-chloro-2- N Cl pyridinyl Me CH₂CN OEt 3-chloro-2- N Clpyridinyl Et CH₂CN OEt 3-chloro-2- N Cl pyridinyl CH₂CN CH₂CN OEt3-chloro-2- N Cl pyridinyl CH₂CH₂OMe H OEt 3-chloro-2- N Cl pyridinyl HCH₂CH₂OMe OEt 3-chloro-2- N Cl pyridinyl CH₂CH₂OMe CH₂CH₂OMe OEt3-chloro-2- N Cl pyridinyl CH₂CH₂SMe H OEt 3-chloro-2- N Cl pyridinyl HCH₂CH₂SMe OEt 3-chloro-2- N Cl pyridinyl Me CO₂Me OEt 3-chloro-2- N Clpyridinyl Et CO₂Me OEt 3-chloro-2- N Cl pyridinyl H 2- OEt 3-chloro-2- NCl pyridinyl pyridinyl H 3- OEt 3-chloro-2- N Cl pyridinyl pyridinyl H4- OEt 3-chloro-2- N Cl pyridinyl pyridinyl —(CH₂)₃— OEt 3-chloro-2- NCl pyridinyl —(CH₂)₄— OEt 3-chloro-2- N Cl pyridinyl —CH₂NHCH₂— OEt3-chloro-2- N Cl pyridinyl —CH₂NMeCH₂— OEt 3-chloro-2- N Cl pyridinyl—CH₂N(iso-Pr)CH₂— OEt 3-chloro-2- N Cl pyridinyl —CH₂N(CHO)CH₂— OEt3-chloro-2- N Cl pyridinyl —CH₂N(Ac)CH₂— OEt 3-chloro-2- N Cl pyridinyl—CH₂N(CO₂Me)CH₂— OEt 3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Et)CH₂— OEt3-chloro-2- N Cl pyridinyl H H OEt 3-chloro-2- N Br pyridinyl Me H OEt3-chloro-2- N Br pyridinyl H Me OEt 3-chloro-2- N Br pyridinyl Me Me OEt3-chloro-2- N Br pyridinyl Et H OEt 3-chloro-2- N Br pyridinyl H Et OEt3-chloro-2- N Br pyridinyl Et Et OEt 3-chloro-2- N Br pyridinyl n-Pr HOEt 3-chloro-2- N Br pyridinyl H n-Pr OEt 3-chloro-2- N Br pyridinyliso-Pr H OEt 3-chloro-2- N Br pyridinyl H iso-Pr OEt 3-chloro-2- N Brpyridinyl iso-Bu H OEt 3-chloro-2- N Br pyridinyl H iso-Bu OEt3-chloro-2- N Br pyridinyl tert-Bu H OEt 3-chloro-2- N Br pyridinyl Htert-Bu OEt 3-chloro-2- N Br pyridinyl CH₂CF₃ H OEt 3-chloro-2- N Brpyridinyl H CH₂CF₃ OEt 3-chloro-2- N Br pyridinyl CH₂CN H OEt3-chloro-2- N Br pyridinyl H CH₂CN OEt 3-chloro-2- N Br pyridinyl CH₂OMeH OEt 3-chloro-2- N Br pyridinyl H CH₂OMe OEt 3-chloro-2- N Br pyridinylCH₂CH═CH₂ H OEt 3-chloro-2- N Br pyridinyl H CH₂CH═CH₂ OEt 3-chloro-2- NBr pyridinyl CH₂CCH H OEt 3-chloro-2- N Br pyridinyl H CH₂CCH OEt3-chloro-2- N Br pyridinyl H CO₂Me OEt 3-chloro-2- N Br pyridinyl Me EtOEt 3-chloro-2- N Br pyridinyl Et Me OEt 3-chloro-2- N Br pyridinylCH₂CH═CH₂ Me OEt 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ Et OEt 3-chloro-2-N Br pyridinyl Me CH₂CH═CH₂ OEt 3-chloro-2- N Br pyridinyl Et CH₂CH═CH₂OEt 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ CH₂CH═CH₂ OEt 3-chloro-2- N Brpyridinyl CH₂CCH Me OEt 3-chloro-2- N Br pyridinyl CH₂CCH Et OEt3-chloro-2- N Br pyridinyl Me CH₂CCH OEt 3-chloro-2- N Br pyridinyl EtCH₂CCH OEt 3-chloro-2- N Br pyridinyl CH₂CCH CH₂CCH OEt 3-chloro-2- N Brpyridinyl cyc-Pr H OEt 3-chloro-2- N Br pyridinyl H cyc-Pr OEt3-chloro-2- N Br pyridinyl iso-Bu iso-Bu OEt 3-chloro-2- N Br pyridinylsec-Bu H OEt 3-chloro-2- N Br pyridinyl H sec-Bu OEt 3-chloro-2- N Brpyridinyl cyc-Bu H OEt 3-chloro-2- N Br pyridinyl H cyc-Bu OEt3-chloro-2- N Br pyridinyl CH₂₋cyc-Pr H OEt 3-chloro-2- N Br pyridinyl HCH₂₋cyc-Pr OEt 3-chloro-2- N Br pyridinyl CH₂₋cyc-Bu H OEt 3-chloro-2- NBr pyridinyl H CH₂₋cyc-Bu OEt 3-chloro-2- N Br pyridinyl CH₂CF₃ Me OEt3-chloro-2- N Br pyridinyl CH₂CF₃ Et OEt 3-chloro-2- N Br pyridinyl MeCH₂CF₃ OEt 3-chloro-2- N Br pyridinyl Et CH₂CF₃ OEt 3-chloro-2- N Brpyridinyl CH₂CF₃ CH₂CF₃ OEt 3-chloro-2- N Br pyridinyl CH₂CN Me OEt3-chloro-2- N Br pyridinyl CH₂CN Et OEt 3-chloro-2- N Br pyridinyl MeCH₂CN OEt 3-chloro-2- N Br pyridinyl Et CH₂CN OEt 3-chloro-2- N Brpyridinyl CH₂CN CH₂CN OEt 3-chloro-2- N Br pyridinyl CH₂CH₂OMe H OEt3-chloro-2- N Br pyridinyl H CH₂CH₂OMe OEt 3-chloro-2- N Br pyridinylCH₂CH₂OMe CH₂CH₂OMe OEt 3-chloro-2- N Br pyridinyl CH₂CH₂SMe H OEt3-chloro-2- N Br pyridinyl H CH₂CH₂SMe OEt 3-chloro-2- N Br pyridinyl MeCO₂Me OEt 3-chloro-2- N Br pyridinyl Et CO₂Me OEt 3-chloro-2- N Brpyridinyl H 2- OEt 3-chloro-2- N Br pyridinyl pyridinyl H 3- OEt3-chloro-2- N Br pyridinyl pyridinyl H 4- OEt 3-chloro-2- N Br pyridinylpyridinyl —(CH₂)₃— OEt 3-chloro-2- N Br pyridinyl —(CH₂)₄— OEt3-chloro-2- N Br pyridinyl —CH₂NHCH₂— OEt 3-chloro-2- N Br pyridinyl—CH₂NMeCH₂— OEt 3-chloro-2- N Br pyridinyl —CH₂N(iso-Pr)CH₂— OEt3-chloro-2- N Br pyridinyl —CH₂N(CHO)CH₂— OEt 3-chloro-2- N Br pyridinyl—CH₂N(Ac)CH₂— OEt 3-chloro-2- N Br pyridinyl —CH₂N(CO₂Me)CH₂— OEt3-chloro-2- N Br pyridinyl —CH₂N(CO₂Et)CH₂— OEt 3-chloro-2- N Brpyridinyl H H OEt 3-chloro-2- N CF₃ pyridinyl Me H OEt 3-chloro-2- N CF₃pyridinyl H Me OEt 3-chloro-2- N CF₃ pyridinyl Me Me OEt 3-chloro-2- NCF₃ pyridinyl Et H OEt 3-chloro-2- N CF₃ pyridinyl H Et OEt 3-chloro-2-N CF₃ pyridinyl Et Et OEt 3-chloro-2- N CF₃ pyridinyl n-Pr H OEt3-chloro-2- N CF₃ pyridinyl H n-Pr OEt 3-chloro-2- N CF₃ pyridinyliso-Pr H OEt 3-chloro-2- N CF₃ pyridinyl H iso-Pr OEt 3-chloro-2- N CF₃pyridinyl iso-Bu H OEt 3-chloro-2- N CF₃ pyridinyl H iso-Bu OEt3-chloro-2- N CF₃ pyridinyl tert-Bu H OEt 3-chloro-2- N CF₃ pyridinyl Htert-Bu OEt 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ H OEt 3-chloro-2- N CF₃pyridinyl H CH₂CF₃ OEt 3-chloro-2- N CF₃ pyridinyl CH₂CN H OEt3-chloro-2- N CF₃ pyridinyl H CH₂CN OEt 3-chloro-2- N CF₃ pyridinylCH₂OMe H OEt 3-chloro-2- N CF₃ pyridinyl H CH₂OMe OEt 3-chloro-2- N CF₃pyridinyl CH₂CH═CH₂ H OEt 3-chloro-2- N CF₃ pyridinyl H CH₂CH═CH₂ OEt3-chloro-2- N CF₃ pyridinyl CH₂CCH H OEt 3-chloro-2- N CF₃ pyridinyl HCH₂CCH OEt 3-chloro-2- N CF₃ pyridinyl H CO₂Me OEt 3-chloro-2- N CF₃pyridinyl Me Et OEt 3-chloro-2- N CF₃ pyridinyl Et Me OEt 3-chloro-2- NCF₃ pyridinyl CH₂CH═CH₂ Me OEt 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂ EtOEt 3-chloro-2- N CF₃ pyridinyl Me CH₂CH═CH₂ OEt 3-chloro-2- N CF₃pyridinyl Et CH₂CH═CH₂ OEt 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂CH₂CH═CH₂ OEt 3-chloro-2- N CF₃ pyridinyl CH₂CCH Me OEt 3-chloro-2- NCF₃ pyridinyl CH₂CCH Et OEt 3-chloro-2- N CF₃ pyridinyl Me CH₂CCH OEt3-chloro-2- N CF₃ pyridinyl Et CH₂CCH OEt 3-chloro-2- N CF₃ pyridinylCH₂CCH CH₂CCH OEt 3-chloro-2- N CF₃ pyridinyl cyc-Pr H OEt 3-chloro-2- NCF₃ pyridinyl H cyc-Pr OEt 3-chloro-2- N CF₃ pyridinyl iso-Bu iso-Bu OEt3-chloro-2- N CF₃ pyridinyl sec-Bu H OEt 3-chloro-2- N CF₃ pyridinyl Hsec-Bu OEt 3-chloro-2- N CF₃ pyridinyl cyc-Bu H OEt 3-chloro-2- N CF₃pyridinyl H cyc-Bu OEt 3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Pr H OEt3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Pr OEt 3-chloro-2- N CF₃ pyridinylCH₂₋cyc-Bu H OEt 3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Bu OEt3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Me OEt 3-chloro-2- N CF₃ pyridinylCH₂CF₃ Et OEt 3-chloro-2- N CF₃ pyridinyl Me CH₂CF₃ OEt 3-chloro-2- NCF₃ pyridinyl Et CH₂CF₃ OEt 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ CH₂CF₃OEt 3-chloro-2- N CF₃ pyridinyl CH₂CN Me OEt 3-chloro-2- N CF₃ pyridinylCH₂CN Et OEt 3-chloro-2- N CF₃ pyridinyl Me CH₂CN OEt 3-chloro-2- N CF₃pyridinyl Et CH₂CN OEt 3-chloro-2- N CF₃ pyridinyl CH₂CN CH₂CN OEt3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe H OEt 3-chloro-2- N CF₃ pyridinylH CH₂CH₂OMe OEt 3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe CH₂CH₂OMe OEt3-chloro-2- N CF₃ pyridinyl CH₂CH₂SMe H OEt 3-chloro-2- N CF₃ pyridinylH CH₂CH₂SMe OEt 3-chloro-2- N CF₃ pyridinyl Me CO₂Me OEt 3-chloro-2- NCF₃ pyridinyl Et CO₂Me OEt 3-chloro-2- N CF₃ pyridinyl H 2- OEt3-chloro-2- N CF₃ pyridinyl pyridinyl H 3- OEt 3-chloro-2- N CF₃pyridinyl pyridinyl H 4- OEt 3-chloro-2- N CF₃ pyridinyl pyridinyl—(CH₂)₃— OEt 3-chloro-2- N CF₃ pyridinyl —(CH₂)₄— OEt 3-chloro-2- N CF₃pyridinyl —CH₂NHCH₂— OEt 3-chloro-2- N CF₃ pyridinyl —CH₂NMeCH₂— OEt3-chloro-2- N CF₃ pyridinyl —CH₂N(iso-Pr)CH₂— OEt 3-chloro-2- N CF₃pyridinyl —CH₂N(CHO)CH₂— OEt 3-chloro-2- N CF₃ pyridinyl —CH₂N(Ac)CH₂—OEt 3-chloro-2- N CF₃ pyridinyl —CH₂N(CO₂Me)CH₂— OEt 3-chloro-2- N CF₃pyridinyl —CH₂N(CO₂Et)CH₂— OEt 3-chloro-2- N CF₃ pyridinyl H H NH₂3-chloro-2- N Cl pyridinyl Me H NH₂ 3-chloro-2- N Cl pyridinyl H Me NH₂3-chloro-2- N Cl pyridinyl Me Me NH₂ 3-chloro-2- N Cl pyridinyl Et H NH₂3-chloro-2- N Cl pyridinyl H Et NH₂ 3-chloro-2- N Cl pyridinyl Et Et NH₂3-chloro-2- N Cl pyridinyl n-Pr H NH₂ 3-chloro-2- N Cl pyridinyl H n-PrNH₂ 3-chloro-2- N Cl pyridinyl iso-Pr H NH₂ 3-chloro-2- N Cl pyridinyl Hiso-Pr NH₂ 3-chloro-2- N Cl pyridinyl iso-Bu H NH₂ 3-chloro-2- N Clpyridinyl H iso-Bu NH₂ 3-chloro-2- N Cl pyridinyl tert-Bu H NH₂3-chloro-2- N Cl pyridinyl H tert-Bu NH₂ 3-chloro-2- N Cl pyridinylCH₂CF₃ H NH₂ 3-chloro-2- N Cl pyridinyl H CH₂CF₃ NH₂ 3-chloro-2- N Clpyridinyl CH₂CN H NH₂ 3-chloro-2- N Cl pyridinyl H CH₂CN NH₂ 3-chloro-2-N Cl pyridinyl CH₂OMe H NH₂ 3-chloro-2- N Cl pyridinyl H CH₂OMe NH₂3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ H NH₂ 3-chloro-2- N Cl pyridinyl HCH₂CH═CH₂ NH₂ 3-chloro-2- N Cl pyridinyl CH₂CCH H NH₂ 3-chloro-2- N Clpyridinyl H CH₂CCH NH₂ 3-chloro-2- N Cl pyridinyl H CO₂Me NH₂3-chloro-2- N Cl pyridinyl Me Et NH₂ 3-chloro-2- N Cl pyridinyl Et MeNH₂ 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ Me NH₂ 3-chloro-2- N Clpyridinyl CH₂CH═CH₂ Et NH₂ 3-chloro-2- N Cl pyridinyl Me CH₂CH═CH₂ NH₂3-chloro-2- N Cl pyridinyl Et CH₂CH═CH₂ NH₂ 3-chloro-2- N Cl pyridinylCH₂CH═CH₂ CH₂CH═CH₂ NH₂ 3-chloro-2- N Cl pyridinyl CH₂CCH Me NH₂3-chloro-2- N Cl pyridinyl CH₂CCH Et NH₂ 3-chloro-2- N Cl pyridinyl MeCH₂CCH NH₂ 3-chloro-2- N Cl pyridinyl Et CH₂CCH NH₂ 3-chloro-2- N Clpyridinyl CH₂CCH CH₂CCH NH₂ 3-chloro-2- N Cl pyridinyl cyc-Pr H NH₂3-chloro-2- N Cl pyridinyl H cyc-Pr NH₂ 3-chloro-2- N Cl pyridinyliso-Bu iso-Bu NH₂ 3-chloro-2- N Cl pyridinyl sec-Bu H NH₂ 3-chloro-2- NCl pyridinyl H sec-Bu NH₂ 3-chloro-2- N Cl pyridinyl cyc-Bu H NH₂3-chloro-2- N Cl pyridinyl H cyc-Bu NH₂ 3-chloro-2- N Cl pyridinylCH₂₋cyc-Pr H NH₂ 3-chloro-2- N Cl pyridinyl H CH₂₋cyc-Pr NH₂ 3-chloro-2-N Cl pyridinyl CH₂₋cyc-Bu H NH₂ 3-chloro-2- N Cl pyridinyl H CH₂₋cyc-BuNH₂ 3-chloro-2- N Cl pyridinyl CH₂CF₃ Me NH₂ 3-chloro-2- N Cl pyridinylCH₂CF₃ Et NH₂ 3-chloro-2- N Cl pyridinyl Me CH₂CF₃ NH₂ 3-chloro-2- N Clpyridinyl Et CH₂CF₃ NH₂ 3-chloro-2- N Cl pyridinyl CH₂CF₃ CH₂CF₃ NH₂3-chloro-2- N Cl pyridinyl CH₂CN Me NH₂ 3-chloro-2- N Cl pyridinyl CH₂CNEt NH₂ 3-chloro-2- N Cl pyridinyl Me CH₂CN NH₂ 3-chloro-2- N Clpyridinyl Et CH₂CN NH₂ 3-chloro-2- N Cl pyridinyl CH₂CN CH₂CN NH₂3-chloro-2- N Cl pyridinyl CH₂CH₂OMe H NH₂ 3-chloro-2- N Cl pyridinyl HCH₂CH₂OMe NH₂ 3-chloro-2- N Cl pyridinyl CH₂CH₂OMe CH₂CH₂OMe NH₂3-chloro-2- N Cl pyridinyl CH₂CH₂SMe H NH₂ 3-chloro-2- N Cl pyridinyl HCH₂CH₂SMe NH₂ 3-chloro-2- N Cl pyridinyl Me CO₂Me NH₂ 3-chloro-2- N Clpyridinyl Et CO₂Me NH₂ 3-chloro-2- N Cl pyridinyl H 2- NH₂ 3-chloro-2- NCl pyridinyl pyridinyl H 3- NH₂ 3-chloro-2- N Cl pyridinyl pyridinyl H4- NH₂ 3-chloro-2- N Cl pyridinyl pyridinyl —(CH₂)₃— NH₂ 3-chloro-2- NCl pyridinyl —(CH₂)₄— NH₂ 3-chloro-2- N Cl pyridinyl —CH₂NHCH₂— NH₂3-chloro-2- N Cl pyridinyl —CH₂NMeCH₂— NH₂ 3-chloro-2- N Cl pyridinyl—CH₂N(iso-Pr)CH₂— NH₂ 3-chloro-2- N Cl pyridinyl —CH₂N(CHO)CH₂— NH₂3-chloro-2- N Cl pyridinyl —CH₂N(Ac)CH₂— NH₂ 3-chloro-2- N Cl pyridinyl—CH₂N(CO₂Me)CH₂— NH₂ 3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Et)CH₂— NH₂3-chloro-2- N Cl pyridinyl H H NH₂ 3-chloro-2- N Br pyridinyl Me H NH₂3-chloro-2- N Br pyridinyl H Me NH₂ 3-chloro-2- N Br pyridinyl Me Me NH₂3-chloro-2- N Br pyridinyl Et H NH₂ 3-chloro-2- N Br pyridinyl H Et NH₂3-chloro-2- N Br pyridinyl Et Et NH₂ 3-chloro-2- N Br pyridinyl n-Pr HNH₂ 3-chloro-2- N Br pyridinyl H n-Pr NH₂ 3-chloro-2- N Br pyridinyliso-Pr H NH₂ 3-chloro-2- N Br pyridinyl H iso-Pr NH₂ 3-chloro-2- N Brpyridinyl iso-Bu H NH₂ 3-chloro-2- N Br pyridinyl H iso-Bu NH₂3-chloro-2- N Br pyridinyl tert-Bu H NH₂ 3-chloro-2- N Br pyridinyl Htert-Bu NH₂ 3-chloro-2- N Br pyridinyl CH₂CF₃ H NH₂ 3-chloro-2- N Brpyridinyl H CH₂CF₃ NH₂ 3-chloro-2- N Br pyridinyl CH₂CN H NH₂3-chloro-2- N Br pyridinyl H CH₂CN NH₂ 3-chloro-2- N Br pyridinyl CH₂OMeH NH₂ 3-chloro-2- N Br pyridinyl H CH₂OMe NH₂ 3-chloro-2- N Br pyridinylCH₂CH═CH₂ H NH₂ 3-chloro-2- N Br pyridinyl H CH₂CH═CH₂ NH₂ 3-chloro-2- NBr pyridinyl CH₂CCH H NH₂ 3-chloro-2- N Br pyridinyl H CH₂CCH NH₂3-chloro-2- N Br pyridinyl H CO₂Me NH₂ 3-chloro-2- N Br pyridinyl Me EtNH₂ 3-chloro-2- N Br pyridinyl Et Me NH₂ 3-chloro-2- N Br pyridinylCH₂CH═CH₂ Me NH₂ 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ Et NH₂ 3-chloro-2-N Br pyridinyl Me CH₂CH═CH₂ NH₂ 3-chloro-2- N Br pyridinyl Et CH₂CH═CH₂NH₂ 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ CH₂CH═CH₂ NH₂ 3-chloro-2- N Brpyridinyl CH₂CCH Me NH₂ 3-chloro-2- N Br pyridinyl CH₂CCH Et NH₂3-chloro-2- N Br pyridinyl Me CH₂CCH NH₂ 3-chloro-2- N Br pyridinyl EtCH₂CCH NH₂ 3-chloro-2- N Br pyridinyl CH₂CCH CH₂CCH NH₂ 3-chloro-2- N Brpyridinyl cyc-Pr H NH₂ 3-chloro-2- N Br pyridinyl H cyc-Pr NH₂3-chloro-2- N Br pyridinyl iso-Bu iso-Bu NH₂ 3-chloro-2- N Br pyridinylsec-Bu H NH₂ 3-chloro-2- N Br pyridinyl H sec-Bu NH₂ 3-chloro-2- N Brpyridinyl cyc-Bu H NH₂ 3-chloro-2- N Br pyridinyl H cyc-Bu NH₂3-chloro-2- N Br pyridinyl CH₂₋cyc-Pr H NH₂ 3-chloro-2- N Br pyridinyl HCH₂₋cyc-Pr NH₂ 3-chloro-2- N Br pyridinyl CH₂₋cyc-Bu H NH₂ 3-chloro-2- NBr pyridinyl H CH₂₋cyc-Bu NH₂ 3-chloro-2- N Br pyridinyl CH₂CF₃ Me NH₂3-chloro-2- N Br pyridinyl CH₂CF₃ Et NH₂ 3-chloro-2- N Br pyridinyl MeCH₂CF₃ NH₂ 3-chloro-2- N Br pyridinyl Et CH₂CF₃ NH₂ 3-chloro-2- N Brpyridinyl CH₂CF₃ CH₂CF₃ NH₂ 3-chloro-2- N Br pyridinyl CH₂CN Me NH₂3-chloro-2- N Br pyridinyl CH₂CN Et NH₂ 3-chloro-2- N Br pyridinyl MeCH₂CN NH₂ 3-chloro-2- N Br pyridinyl Et CH₂CN NH₂ 3-chloro-2- N Brpyridinyl CH₂CN CH₂CN NH₂ 3-chloro-2- N Br pyridinyl CH₂CH₂OMe H NH₂3-chloro-2- N Br pyridinyl H CH₂CH₂OMe NH₂ 3-chloro-2- N Br pyridinylCH₂CH₂OMe CH₂CH₂OMe NH₂ 3-chloro-2- N Br pyridinyl CH₂CH₂SMe H NH₂3-chloro-2- N Br pyridinyl H CH₂CH₂SMe NH₂ 3-chloro-2- N Br pyridinyl MeCO₂Me NH₂ 3-chloro-2- N Br pyridinyl Et CO₂Me NH₂ 3-chloro-2- N Brpyridinyl H 2- NH₂ 3-chloro-2- N Br pyridinyl pyridinyl H 3- NH₂3-chloro-2- N Br pyridinyl pyridinyl H 4- NH₂ 3-chloro-2- N Br pyridinylpyridinyl —(CH₂)₃— NH₂ 3-chloro-2- N Br pyridinyl —(CH₂)₄— NH₂3-chloro-2- N Br pyridinyl —CH₂NHCH₂— NH₂ 3-chloro-2- N Br pyridinyl—CH₂NMeCH₂— NH₂ 3-chloro-2- N Br pyridinyl —CH₂N(iso-Pr)CH₂— NH₂3-chloro-2- N Br pyridinyl —CH₂N(CHO)CH₂— NH₂ 3-chloro-2- N Br pyridinyl—CH₂N(Ac)CH₂— NH₂ 3-chloro-2- N Br pyridinyl —CH₂N(CO₂Me)CH₂— NH₂3-chloro-2- N Br pyridinyl —CH₂N(CO₂Et)CH₂— NH₂ 3-chloro-2- N Brpyridinyl H H NH₂ 3-chloro-2- N CF₃ pyridinyl Me H NH₂ 3-chloro-2- N CF₃pyridinyl H Me NH₂ 3-chloro-2- N CF₃ pyridinyl Me Me NH₂ 3-chloro-2- NCF₃ pyridinyl Et H NH₂ 3-chloro-2- N CF₃ pyridinyl H Et NH₂ 3-chloro-2-N CF₃ pyridinyl Et Et NH₂ 3-chloro-2- N CF₃ pyridinyl n-Pr H NH₂3-chloro-2- N CF₃ pyridinyl H n-Pr NH₂ 3-chloro-2- N CF₃ pyridinyliso-Pr H NH₂ 3-chloro-2- N CF₃ pyridinyl H iso-Pr NH₂ 3-chloro-2- N CF₃pyridinyl iso-Bu H NH₂ 3-chloro-2- N CF₃ pyridinyl H iso-Bu NH₂3-chloro-2- N CF₃ pyridinyl tert-Bu H NH₂ 3-chloro-2- N CF₃ pyridinyl Htert-Bu NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ H NH₂ 3-chloro-2- N CF₃pyridinyl H CH₂CF₃ NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CN H NH₂3-chloro-2- N CF₃ pyridinyl H CH₂CN NH₂ 3-chloro-2- N CF₃ pyridinylCH₂OMe H NH₂ 3-chloro-2- N CF₃ pyridinyl H CH₂OMe NH₂ 3-chloro-2- N CF₃pyridinyl CH₂CH═CH₂ H NH₂ 3-chloro-2- N CF₃ pyridinyl H CH₂CH═CH₂ NH₂3-chloro-2- N CF₃ pyridinyl CH₂CCH H NH₂ 3-chloro-2- N CF₃ pyridinyl HCH₂CCH NH₂ 3-chloro-2- N CF₃ pyridinyl H CO₂Me NH₂ 3-chloro-2- N CF₃pyridinyl Me Et NH₂ 3-chloro-2- N CF₃ pyridinyl Et Me NH₂ 3-chloro-2- NCF₃ pyridinyl CH₂CH═CH₂ Me NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂ EtNH₂ 3-chloro-2- N CF₃ pyridinyl Me CH₂CH═CH₂ NH₂ 3-chloro-2- N CF₃pyridinyl Et CH₂CH═CH₂ NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂CH₂CH═CH₂ NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CCH Me NH₂ 3-chloro-2- NCF₃ pyridinyl CH₂CCH Et NH₂ 3-chloro-2- N CF₃ pyridinyl Me CH₂CCH NH₂3-chloro-2- N CF₃ pyridinyl Et CH₂CCH NH₂ 3-chloro-2- N CF₃ pyridinylCH₂CCH CH₂CCH NH₂ 3-chloro-2- N CF₃ pyridinyl cyc-Pr H NH₂ 3-chloro-2- NCF₃ pyridinyl H cyc-Pr NH₂ 3-chloro-2- N CF₃ pyridinyl iso-Bu iso-Bu NH₂3-chloro-2- N CF₃ pyridinyl sec-Bu H NH₂ 3-chloro-2- N CF₃ pyridinyl Hsec-Bu NH₂ 3-chloro-2- N CF₃ pyridinyl cyc-Bu H NH₂ 3-chloro-2- N CF₃pyridinyl H cyc-Bu NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Pr H NH₂3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Pr NH₂ 3-chloro-2- N CF₃ pyridinylCH₂₋cyc-Bu H NH₂ 3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Bu NH₂3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Me NH₂ 3-chloro-2- N CF₃ pyridinylCH₂CF₃ Et NH₂ 3-chloro-2- N CF₃ pyridinyl Me CH₂CF₃ NH₂ 3-chloro-2- NCF₃ pyridinyl Et CH₂CF₃ NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ CH₂CF₃NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CN Me NH₂ 3-chloro-2- N CF₃ pyridinylCH₂CN Et NH₂ 3-chloro-2- N CF₃ pyridinyl Me CH₂CN NH₂ 3-chloro-2- N CF₃pyridinyl Et CH₂CN NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CN CH₂CN NH₂3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe H NH₂ 3-chloro-2- N CF₃ pyridinylH CH₂CH₂OMe NH₂ 3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe CH₂CH₂OMe NH₂3-chloro-2- N CF₃ pyridinyl CH₂CH₂SMe H NH₂ 3-chloro-2- N CF₃ pyridinylH CH₂CH₂SMe NH₂ 3-chloro-2- N CF₃ pyridinyl Me CO₂Me NH₂ 3-chloro-2- NCF₃ pyridinyl Et CO₂Me NH₂ 3-chloro-2- N CF₃ pyridinyl H 2- NH₂3-chloro-2- N CF₃ pyridinyl pyridinyl H 3- NH₂ 3-chloro-2- N CF₃pyridinyl pyridinyl H 4- NH₂ 3-chloro-2- N CF₃ pyridinyl pyridinyl—(CH₂)₃— NH₂ 3-chloro-2- N CF₃ pyridinyl —(CH₂)₄— NH₂ 3-chloro-2- N CF₃pyridinyl —CH₂NHCH₂— NH₂ 3-chloro-2- N CF₃ pyridinyl —CH₂NMeCH₂— NH₂3-chloro-2- N CF₃ pyridinyl —CH₂N(iso-Pr)CH₂— NH₂ 3-chloro-2- N CF₃pyridinyl —CH₂N(CHO)CH₂— NH₂ 3-chloro-2- N CF₃ pyridinyl —CH₂N(Ac)CH₂—NH₂ 3-chloro-2- N CF₃ pyridinyl —CH₂N(CO₂Me)CH₂— NH₂ 3-chloro-2- N CF₃pyridinyl —CH₂N(CO₂Et)CH₂— NH₂ 3-chloro-2- N CF₃ pyridinyl H H NHMe3-chloro-2- N Cl pyridinyl Me H NHMe 3-chloro-2- N Cl pyridinyl H MeNHMe 3-chloro-2- N Cl pyridinyl Me Me NHMe 3-chloro-2- N Cl pyridinyl EtH NHMe 3-chloro-2- N Cl pyridinyl H Et NHMe 3-chloro-2- N Cl pyridinylEt Et NHMe 3-chloro-2- N Cl pyridinyl n-Pr H NHMe 3-chloro-2- N Clpyridinyl H n-Pr NHMe 3-chloro-2- N Cl pyridinyl iso-Pr H NHMe3-chloro-2- N Cl pyridinyl H iso-Pr NHMe 3-chloro-2- N Cl pyridinyliso-Bu H NHMe 3-chloro-2- N Cl pyridinyl H iso-Bu NHMe 3-chloro-2- N Clpyridinyl tert-Bu H NHMe 3-chloro-2- N Cl pyridinyl H tert-Bu NHMe3-chloro-2- N Cl pyridinyl CH₂CF₃ H NHMe 3-chloro-2- N Cl pyridinyl HCH₂CF₃ NHMe 3-chloro-2- N Cl pyridinyl pyridinyl CH₂CN H NHMe3-chloro-2- N Cl pyridinyl H CH₂CN NHMe 3-chloro-2- N Cl pyridinylCH₂OMe H NHMe 3-chloro-2- N Cl pyridinyl H CH₂OMe NHMe 3-chloro-2- N Clpyridinyl CH₂CH═CH₂ H NHMe 3-chloro-2- N Cl pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- N Cl pyridinyl CH₂CCH H NHMe 3-chloro-2- N Cl pyridinyl HCH₂CCH NHMe 3-chloro-2- N Cl pyridinyl H CO₂Me NHMe 3-chloro-2- N Clpyridinyl Me Et NHMe 3-chloro-2- N Cl pyridinyl Et Me NHMe 3-chloro-2- NCl pyridinyl CH₂CH═CH₂ Me NHMe 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ EtNHMe 3-chloro-2- N Cl pyridinyl Me CH₂CH═CH₂ NHMe 3-chloro-2- N Clpyridinyl Et CH₂CH═CH₂ NHMe 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂CH₂CH═CH₂ NHMe 3-chloro-2- N Cl pyridinyl CH₂CCH Me NHMe 3-chloro-2- NCl pyridinyl CH₂CCH Et NHMe 3-chloro-2- N Cl pyridinyl Me CH₂CCH NHMe3-chloro-2- N Cl pyridinyl Et CH₂CCH NHMe 3-chloro-2- N Cl pyridinylCH₂CCH CH₂CCH NHMe 3-chloro-2- N Cl pyridinyl cyc-Pr H NHMe 3-chloro-2-N Cl pyridinyl H cyc-Pr NHMe 3-chloro-2- N Cl pyridinyl iso-Bu iso-BuNHMe 3-chloro-2- N Cl pyridinyl sec-Bu H NHMe 3-chloro-2- N Cl pyridinylH sec-Bu NHMe 3-chloro-2- N Cl pyridinyl cyc-Bu H NHMe 3-chloro-2- N Clpyridinyl H cyc-Bu NHMe 3-chloro-2- N Cl pyridinyl CH₂₋cyc-Pr H NHMe3-chloro-2- N Cl pyridinyl H CH₂₋cyc-Pr NHMe 3-chloro-2- N Cl pyridinylCH₂₋cyc-Bu H NHMe 3-chloro-2- N Cl pyridinyl H CH₂₋cyc-Bu NHMe3-chloro-2- N Cl pyridinyl CH₂CF₃ Me NHMe 3-chloro-2- N Cl pyridinylCH₂CF₃ Et NHMe 3-chloro-2- N Cl pyridinyl Me CH₂CF₃ NHMe 3-chloro-2- NCl pyridinyl Et CH₂CF₃ NHMe 3-chloro-2- N Cl pyridinyl CH₂CF₃ CH₂CF₃NHMe 3-chloro-2- N Cl pyridinyl CH₂CN Me NHMe 3-chloro-2- N Cl pyridinylCH₂CN Et NHMe 3-chloro-2- N Cl pyridinyl Me CH₂CN NHMe 3-chloro-2- N Clpyridinyl Et CH₂CN NHMe 3-chloro-2- N Cl pyridinyl CH₂CN CH₂CN NHMe3-chloro-2- N Cl pyridinyl CH₂CH₂OMe H NHMe 3-chloro-2- N Cl pyridinyl HCH₂CH₂OMe NHMe 3-chloro-2- N Cl pyridinyl CH₂CH₂OMe CH₂CH₂OMe NHMe3-chloro-2- N Cl pyridinyl CH₂CH₂SMe H NHMe 3-chloro-2- N Cl pyridinyl HCH₂CH₂SMe NHMe 3-chloro-2- N Cl pyridinyl Me CO₂Me NHMe 3-chloro-2- N Clpyridinyl Et CO₂Me NHMe 3-chloro-2- N Cl pyridinyl H 2- NHMe 3-chloro-2-N Cl pyridinyl pyridinyl H 3- NHMe 3-chloro-2- N Cl pyridinyl pyridinylH 4- NHMe 3-chloro-2- N Cl pyridinyl pyridinyl —(CH₂)₃— NHMe 3-chloro-2-N Cl pyridinyl —(CH₂)₄— NHMe 3-chloro-2- N Cl pyridinyl —CH₂NHCH₂— NHMe3-chloro-2- N Cl pyridinyl —CH₂NMeCH₂— NHMe 3-chloro-2- N Cl pyridinyl—CH₂N(iso-Pr)CH₂— NHMe 3-chloro-2- N Cl pyridinyl —CH₂N(CHO)CH₂— NHMe3-chloro-2- N Cl pyridinyl —CH₂N(Ac)CH₂— NHMe 3-chloro-2- N Cl pyridinyl—CH₂N(CO₂Me)CH₂— NHMe 3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Et)CH₂— NHMe3-chloro-2- N Cl pyridinyl H H NHMe 3-chloro-2- N Br pyridinyl Me H NHMe3-chloro-2- N Br pyridinyl H Me NHMe 3-chloro-2- N Br pyridinyl Me MeNHMe 3-chloro-2- N Br pyridinyl Et H NHMe 3-chloro-2- N Br pyridinyl HEt NHMe 3-chloro-2- N Br pyridinyl Et Et NHMe 3-chloro-2- N Br pyridinyln-Pr H NHMe 3-chloro-2- N Br pyridinyl H n-Pr NHMe 3-chloro-2- N Brpyridinyl iso-Pr H NHMe 3-chloro-2- N Br pyridinyl H iso-Pr NHMe3-chloro-2- N Br pyridinyl iso-Bu H NHMe 3-chloro-2- N Br pyridinyl Hiso-Bu NHMe 3-chloro-2- N Br pyridinyl tert-Bu H NHMe 3-chloro-2- N Brpyridinyl H tert-Bu NHMe 3-chloro-2- N Br pyridinyl CH₂CF₃ H NHMe3-chloro-2- N Br pyridinyl H CH₂CF₃ NHMe 3-chloro-2- N Br pyridinylCH₂CN H NHMe 3-chloro-2- N Br pyridinyl H CH₂CN NHMe 3-chloro-2- N Brpyridinyl CH₂OMe H NHMe 3-chloro-2- N Br pyridinyl H CH₂OMe NHMe3-chloro-2- N Br pyridinyl CH₂CH═CH₂ H NHMe 3-chloro-2- N Br pyridinyl HCH₂CH═CH₂ NHMe 3-chloro-2- N Br pyridinyl CH₂CCH H NHMe 3-chloro-2- N Brpyridinyl H CH₂CCH NHMe 3-chloro-2- N Br pyridinyl H CO₂Me NHMe3-chloro-2- N Br pyridinyl Me Et NHMe 3-chloro-2- N Br pyridinyl Et MeNHMe 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ Me NHMe 3-chloro-2- N Brpyridinyl CH₂CH═CH₂ Et NHMe 3-chloro-2- N Br pyridinyl Me CH₂CH═CH₂ NHMe3-chloro-2- N Br pyridinyl Et CH₂CH═CH₂ NHMe 3-chloro-2- N Br pyridinylCH₂CH═CH₂ CH₂CH═CH₂ NHMe 3-chloro-2- N Br pyridinyl CH₂CCH Me NHMe3-chloro-2- N Br pyridinyl CH₂CCH Et NHMe 3-chloro-2- N Br pyridinyl MeCH₂CCH NHMe 3-chloro-2- N Br pyridinyl Et CH₂CCH NHMe 3-chloro-2- N Brpyridinyl CH₂CCH CH₂CCH NHMe 3-chloro-2- N Br pyridinyl cyc-Pr H NHMe3-chloro-2- N Br pyridinyl H cyc-Pr NHMe 3-chloro-2- N Br pyridinyliso-Bu iso-Bu NHMe 3-chloro-2- N Br pyridinyl sec-Bu H NHMe 3-chloro-2-N Br pyridinyl H sec-Bu NHMe 3-chloro-2- N Br pyridinyl cyc-Bu H NHMe3-chloro-2- N Br pyridinyl H cyc-Bu NHMe 3-chloro-2- N Br pyridinylCH₂₋cyc-Pr H NHMe 3-chloro-2- N Br pyridinyl H CH₂₋cyc-Pr NHMe3-chloro-2- N Br pyridinyl CH₂₋cyc-Bu H NHMe 3-chloro-2- N Br pyridinylH CH₂₋cyc-Bu NHMe 3-chloro-2- N Br pyridinyl CH₂CF₃ Me NHMe 3-chloro-2-N Br pyridinyl CH₂CF₃ Et NHMe 3-chloro-2- N Br pyridinyl Me CH₂CF₃ NHMe3-chloro-2- N Br pyridinyl Et CH₂CF₃ NHMe 3-chloro-2- N Br pyridinylCH₂CF₃ CH₂CF₃ NHMe 3-chloro-2- N Br pyridinyl CH₂CN Me NHMe 3-chloro-2-N Br pyridinyl CH₂CN Et NHMe 3-chloro-2- N Br pyridinyl Me CH₂CN NHMe3-chloro-2- N Br pyridinyl Et CH₂CN NHMe 3-chloro-2- N Br pyridinylCH₂CN CH₂CN NHMe 3-chloro-2- N Br pyridinyl CH₂CH₂OMe H NHMe 3-chloro-2-N Br pyridinyl H CH₂CH₂OMe NHMe 3-chloro-2- N Br pyridinyl CH₂CH₂OMeCH₂CH₂OMe NHMe 3-chloro-2- N Br pyridinyl CH₂CH₂SMe H NHMe 3-chloro-2- NBr pyridinyl H CH₂CH₂SMe NHMe 3-chloro-2- N Br pyridinyl Me CO₂Me NHMe3-chloro-2- N Br pyridinyl Et CO₂Me NHMe 3-chloro-2- N Br pyridinyl H 2-NHMe 3-chloro-2- N Br pyridinyl pyridinyl H 3- NHMe 3-chloro-2- N Brpyridinyl pyridinyl H 4- NHMe 3-chloro-2- N Br pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- N Br pyridinyl —(CH₂)₄— NHMe 3-chloro-2- N Brpyridinyl —CH₂NHCH₂— NHMe 3-chloro-2- N Br pyridinyl —CH₂NMeCH₂— NHMe3-chloro-2- N Br pyridinyl —CH₂N(iso-Pr)CH₂— NHMe 3-chloro-2- N Brpyridinyl —CH₂N(CHO)CH₂— NHMe 3-chloro-2- N Br pyridinyl —CH₂N(Ac)CH₂—NHMe 3-chloro-2- N Br pyridinyl —CH₂N(CO₂Me)CH₂— NHMe 3-chloro-2- N Brpyridinyl —CH₂N(CO₂Et)CH₂— NHMe 3-chloro-2- N Br pyridinyl H H NHMe3-chloro-2- N CF₃ pyridinyl Me H NHMe 3-chloro-2- N CF₃ pyridinyl H MeNHMe 3-chloro-2- N CF₃ pyridinyl Me Me NHMe 3-chloro-2- N CF₃ pyridinylEt H NHMe 3-chloro-2- N CF₃ pyridinyl H Et NHMe 3-chloro-2- N CF₃pyridinyl Et Et NHMe 3-chloro-2- N CF₃ pyridinyl n-Pr H NHMe 3-chloro-2-N CF₃ pyridinyl H n-Pr NHMe 3-chloro-2- N CF₃ pyridinyl iso-Pr H NHMe3-chloro-2- N CF₃ pyridinyl H iso-Pr NHMe 3-chloro-2- N CF₃ pyridinyliso-Bu H NHMe 3-chloro-2- N CF₃ pyridinyl H iso-Bu NHMe 3-chloro-2- NCF₃ pyridinyl tert-Bu H NHMe 3-chloro-2- N CF₃ pyridinyl H tert-Bu NHMe3-chloro-2- N CF₃ pyridinyl CH₂CF₃ H NHMe 3-chloro-2- N CF₃ pyridinyl HCH₂CF₃ NHMe 3-chloro-2- N CF₃ pyridinyl CH₂CN H NHMe 3-chloro-2- N CF₃pyridinyl H CH₂CN NHMe 3-chloro-2- N CF₃ pyridinyl CH₂OMe H NHMe3-chloro-2- N CF₃ pyridinyl H CH₂OMe NHMe 3-chloro-2- N CF₃ pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- N CF₃ pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- N CF₃ pyridinyl CH₂CCH H NHMe 3-chloro-2- N CF₃ pyridinyl HCH₂CCH NHMe 3-chloro-2- N CF₃ pyridinyl H CO₂Me NHMe 3-chloro-2- N CF₃pyridinyl Me Et NHMe 3-chloro-2- N CF₃ pyridinyl Et Me NHMe 3-chloro-2-N CF₃ pyridinyl CH₂CH═CH₂ Me NHMe 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂Et NHMe 3-chloro-2- N CF₃ pyridinyl Me CH₂CH═CH₂ NHMe 3-chloro-2- N CF₃pyridinyl Et CH₂CH═CH₂ NHMe 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂CH₂CH═CH₂ NHMe 3-chloro-2- N CF₃ pyridinyl CH₂CCH Me NHMe 3-chloro-2- NCF₃ pyridinyl CH₂CCH Et NHMe 3-chloro-2- N CF₃ pyridinyl Me CH₂CCH NHMe3-chloro-2- N CF₃ pyridinyl Et CH₂CCH NHMe 3-chloro-2- N CF₃ pyridinylCH₂CCH CH₂CCH NHMe 3-chloro-2- N CF₃ pyridinyl cyc-Pr H NHMe 3-chloro-2-N CF₃ pyridinyl H cyc-Pr NHMe 3-chloro-2- N CF₃ pyridinyl iso-Bu iso-BuNHMe 3-chloro-2- N CF₃ pyridinyl sec-Bu H NHMe 3-chloro-2- N CF₃pyridinyl H sec-Bu NHMe 3-chloro-2- N CF₃ pyridinyl cyc-Bu H NHMe3-chloro-2- N CF₃ pyridinyl H cyc-Bu NHMe 3-chloro-2- N CF₃ pyridinylCH₂₋cyc-Pr H NHMe 3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Pr NHMe3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Bu H NHMe 3-chloro-2- N CF₃pyridinyl H CH₂₋cyc-Bu NHMe 3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Me NHMe3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Et NHMe 3-chloro-2- N CF₃ pyridinylMe CH₂CF₃ NHMe 3-chloro-2- N CF₃ pyridinyl Et CH₂CF₃ NHMe 3-chloro-2- NCF₃ pyridinyl CH₂CF₃ CH₂CF₃ NHMe 3-chloro-2- N CF₃ pyridinyl CH₂CN MeNHMe 3-chloro-2- N CF₃ pyridinyl CH₂CN Et NHMe 3-chloro-2- N CF₃pyridinyl Me CH₂CN NHMe 3-chloro-2- N CF₃ pyridinyl Et CH₂CN NHMe3-chloro-2- N CF₃ pyridinyl CH₂CN CH₂CN NHMe 3-chloro-2- N CF₃ pyridinylCH₂CH₂OMe H NHMe 3-chloro-2- N CF₃ pyridinyl H CH₂CH₂OMe NHMe3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe CH₂CH₂OMe NHMe 3-chloro-2- N CF₃pyridinyl CH₂CH₂SMe H NHMe 3-chloro-2- N CF₃ pyridinyl H CH₂CH₂SMe NHMe3-chloro-2- N CF₃ pyridinyl Me CO₂Me NHMe 3-chloro-2- N CF₃ pyridinyl EtCO₂Me NHMe 3-chloro-2- N CF₃ pyridinyl H 2- NHMe 3-chloro-2- N CF₃pyridinyl pyridinyl H 3- NHMe 3-chloro-2- N CF₃ pyridinyl pyridinyl H 4-NHMe 3-chloro-2- N CF₃ pyridinyl pyridinyl —(CH₂)₃— NHMe 3-chloro-2- NCF₃ pyridinyl —(CH₂)₄— NHMe 3-chloro-2- N CF₃ pyridinyl —CH₂NHCH₂— NHMe3-chloro-2- N CF₃ pyridinyl —CH₂NMeCH₂— NHMe 3-chloro-2- N CF₃ pyridinyl—CH₂N(iso-Pr)CH₂— NHMe 3-chloro-2- N CF₃ pyridinyl —CH₂N(CHO)CH₂— NHMe3-chloro-2- N CF₃ pyridinyl —CH₂N(Ac)CH₂— NHMe 3-chloro-2- N CF₃pyridinyl —CH₂N(CO₂Me)CH₂— NHMe 3-chloro-2- N CF₃ pyridinyl—CH₂N(CO₂Et)CH₂— NHMe 3-chloro-2- N CF₃ pyridinyl H H NMe₂ 3-chloro-2- NCl pyridinyl Me H NMe₂ 3-chloro-2- N Cl pyridinyl H Me NMe₂ 3-chloro-2-N Cl pyridinyl Me Me NMe₂ 3-chloro-2- N Cl pyridinyl Et H NMe₂3-chloro-2- N Cl pyridinyl H Et NMe₂ 3-chloro-2- N Cl pyridinyl Et EtNMe₂ 3-chloro-2- N Cl pyridinyl n-Pr H NMe₂ 3-chloro-2- N Cl pyridinyl Hn-Pr NMe₂ 3-chloro-2- N Cl pyridinyl iso-Pr H NMe₂ 3-chloro-2- N Clpyridinyl H iso-Pr NMe₂ 3-chloro-2- N Cl pyridinyl iso-Bu H NMe₂3-chloro-2- N Cl pyridinyl H iso-Bu NMe₂ 3-chloro-2- N Cl pyridinyltert-Bu H NMe₂ 3-chloro-2- N Cl pyridinyl H tert-Bu NMe₂ 3-chloro-2- NCl pyridinyl CH₂CF₃ H NMe₂ 3-chloro-2- N Cl pyridinyl H CH₂CF₃ NMe₂3-chloro-2- N Cl pyridinyl CH₂CN H NMe₂ 3-chloro-2- N Cl pyridinyl HCH₂CN NMe₂ 3-chloro-2- N Cl pyridinyl CH₂OMe H NMe₂ 3-chloro-2- N Clpyridinyl H CH₂OMe NMe₂ 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ H NMe₂3-chloro-2- N Cl pyridinyl H CH₂CH═CH₂ NMe₂ 3-chloro-2- N Cl pyridinylCH₂CCH H NMe₂ 3-chloro-2- N Cl pyridinyl H CH₂CCH NMe₂ 3-chloro-2- N Clpyridinyl H CO₂Me NMe₂ 3-chloro-2- N Cl pyridinyl Me Et NMe₂ 3-chloro-2-N Cl pyridinyl Et Me NMe₂ 3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ Me NMe₂3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ Et NMe₂ 3-chloro-2- N Cl pyridinylMe CH₂CH═CH₂ NMe₂ 3-chloro-2- N Cl pyridinyl Et CH₂CH═CH₂ NMe₂3-chloro-2- N Cl pyridinyl CH₂CH═CH₂ CH₂CH═CH₂ NMe₂ 3-chloro-2- N Clpyridinyl CH₂CCH Me NMe₂ 3-chloro-2- N Cl pyridinyl CH₂CCH Et NMe₂3-chloro-2- N Cl pyridinyl Me CH₂CCH NMe₂ 3-chloro-2- N Cl pyridinyl EtCH₂CCH NMe₂ 3-chloro-2- N Cl pyridinyl CH₂CCH CH₂CCH NMe₂ 3-chloro-2- NCl pyridinyl cyc-Pr H NMe₂ 3-chloro-2- N Cl pyridinyl H cyc-Pr NMe₂3-chloro-2- N Cl pyridinyl iso-Bu iso-Bu NMe₂ 3-chloro-2- N Cl pyridinylsec-Bu H NMe₂ 3-chloro-2- N Cl pyridinyl H sec-Bu NMe₂ 3-chloro-2- N Clpyridinyl cyc-Bu H NMe₂ 3-chloro-2- N Cl pyridinyl H cyc-Bu NMe₂3-chloro-2- N Cl pyridinyl CH₂₋cyc-Pr H NMe₂ 3-chloro-2- N Cl pyridinylH CH₂₋cyc-Pr NMe₂ 3-chloro-2- N Cl pyridinyl CH₂₋cyc-Bu H NMe₂3-chloro-2- N Cl pyridinyl H CH₂₋cyc-Bu NMe₂ 3-chloro-2- N Cl pyridinylCH₂CF₃ Me NMe₂ 3-chloro-2- N Cl pyridinyl CH₂CF₃ Et NMe₂ 3-chloro-2- NCl pyridinyl Me CH₂CF₃ NMe₂ 3-chloro-2- N Cl pyridinyl Et CH₂CF₃ NMe₂3-chloro-2- N Cl pyridinyl CH₂CF₃ CH₂CF₃ NMe₂ 3-chloro-2- N Cl pyridinylCH₂CN Me NMe₂ 3-chloro-2- N Cl pyridinyl CH₂CN Et NMe₂ 3-chloro-2- N Clpyridinyl Me CH₂CN NMe₂ 3-chloro-2- N Cl pyridinyl Et CH₂CN NMe₂3-chloro-2- N Cl pyridinyl CH₂CN CH₂CN NMe₂ 3-chloro-2- N Cl pyridinylCH₂CH₂OMe H NMe₂ 3-chloro-2- N Cl pyridinyl H CH₂CH₂OMe NMe₂ 3-chloro-2-N Cl pyridinyl CH₂CH₂OMe CH₂CH₂OMe NMe₂ 3-chloro-2- N Cl pyridinylCH₂CH₂SMe H NMe₂ 3-chloro-2- N Cl pyridinyl H CH₂CH₂SMe NMe₂ 3-chloro-2-N Cl pyridinyl Me CO₂Me NMe₂ 3-chloro-2- N Cl pyridinyl Et CO₂Me NMe₂3-chloro-2- N Cl pyridinyl H 2- NMe₂ 3-chloro-2- N Cl pyridinylpyridinyl H 3- NMe₂ 3-chloro-2- N Cl pyridinyl pyridinyl H 4- NMe₂3-chloro-2- N Cl pyridinyl pyridinyl —(CH₂)₃— NMe₂ 3-chloro-2- N Clpyridinyl —(CH₂)₄— NMe₂ 3-chloro-2- N Cl pyridinyl —CH₂NHCH₂— NMe₂3-chloro-2- N Cl pyridinyl —CH₂NMeCH₂— NMe₂ 3-chloro-2- N Cl pyridinyl—CH₂N(iso-Pr)CH₂— NMe₂ 3-chloro-2- N Cl pyridinyl —CH₂N(CHO)CH₂— NMe₂3-chloro-2- N Cl pyridinyl —CH₂N(Ac)CH₂— NMe₂ 3-chloro-2- N Cl pyridinyl—CH₂N(CO₂Me)CH₂— NMe₂ 3-chloro-2- N Cl pyridinyl —CH₂N(CO₂Et)CH₂— NMe₂3-chloro-2- N Cl pyridinyl H H NMe₂ 3-chloro-2- N Br pyridinyl Me H NMe₂3-chloro-2- N Br pyridinyl H Me NMe₂ 3-chloro-2- N Br pyridinyl Me MeNMe₂ 3-chloro-2- N Br pyridinyl Et H NMe₂ 3-chloro-2- N Br pyridinyl HEt NMe₂ 3-chloro-2- N Br pyridinyl Et Et NMe₂ 3-chloro-2- N Br pyridinyln-Pr H NMe₂ 3-chloro-2- N Br pyridinyl H n-Pr NMe₂ 3-chloro-2- N Brpyridinyl iso-Pr H NMe₂ 3-chloro-2- N Br pyridinyl H iso-Pr NMe₂3-chloro-2- N Br pyridinyl iso-Bu H NMe₂ 3-chloro-2- N Br pyridinyl Hiso-Bu NMe₂ 3-chloro-2- N Br pyridinyl tert-Bu H NMe₂ 3-chloro-2- N Brpyridinyl H tert-Bu NMe₂ 3-chloro-2- N Br pyridinyl CH₂CF₃ H NMe₂3-chloro-2- N Br pyridinyl H CH₂CF₃ NMe₂ 3-chloro-2- N Br pyridinylCH₂CN H NMe₂ 3-chloro-2- N Br pyridinyl H CH₂CN NMe₂ 3-chloro-2- N Brpyridinyl CH₂OMe H NMe₂ 3-chloro-2- N Br pyridinyl H CH₂OMe NMe₂3-chloro-2- N Br pyridinyl CH₂CH═CH₂ H NMe₂ 3-chloro-2- N Br pyridinyl HCH₂CH═CH₂ NMe₂ 3-chloro-2- N Br pyridinyl CH₂CCH H NMe₂ 3-chloro-2- N Brpyridinyl H CH₂CCH NMe₂ 3-chloro-2- N Br pyridinyl H CO₂Me NMe₂3-chloro-2- N Br pyridinyl Me Et NMe₂ 3-chloro-2- N Br pyridinyl Et MeNMe₂ 3-chloro-2- N Br pyridinyl CH₂CH═CH₂ Me NMe₂ 3-chloro-2- N Brpyridinyl CH₂CH═CH₂ Et NMe₂ 3-chloro-2- N Br pyridinyl Me CH₂CH═CH₂ NMe₂3-chloro-2- N Br pyridinyl Et CH₂CH═CH₂ NMe₂ 3-chloro-2- N Br pyridinylCH₂CH═CH₂ CH₂CH═CH₂ NMe₂ 3-chloro-2- N Br pyridinyl CH₂CCH Me NMe₂3-chloro-2- N Br pyridinyl CH₂CCH Et NMe₂ 3-chloro-2- N Br pyridinyl MeCH₂CCH NMe₂ 3-chloro-2- N Br pyridinyl Et CH₂CCH NMe₂ 3-chloro-2- N Brpyridinyl CH₂CCH CH₂CCH NMe₂ 3-chloro-2- N Br pyridinyl cyc-Pr H NMe₂3-chloro-2- N Br pyridinyl H cyc-Pr NMe₂ 3-chloro-2- N Br pyridinyliso-Bu iso-Bu NMe₂ 3-chloro-2- N Br pyridinyl sec-Bu H NMe₂ 3-chloro-2-N Br pyridinyl H sec-Bu NMe₂ 3-chloro-2- N Br pyridinyl cyc-Bu H NMe₂3-chloro-2- N Br pyridinyl H cyc-Bu NMe₂ 3-chloro-2- N Br pyridinylCH₂₋cyc-Pr H NMe₂ 3-chloro-2- N Br pyridinyl H CH₂₋cyc-Pr NMe₂3-chloro-2- N Br pyridinyl CH₂₋cyc-Bu H NMe₂ 3-chloro-2- N Br pyridinylH CH₂₋cyc-Bu NMe₂ 3-chloro-2- N Br pyridinyl CH₂CF₃ Me NMe₂ 3-chloro-2-N Br pyridinyl CH₂CF₃ Et NMe₂ 3-chloro-2- N Br pyridinyl Me CH₂CF₃ NMe₂3-chloro-2- N Br pyridinyl Et CH₂CF₃ NMe₂ 3-chloro-2- N Br pyridinylCH₂CF₃ CH₂CF₃ NMe₂ 3-chloro-2- N Br pyridinyl CH₂CN Me NMe₂ 3-chloro-2-N Br pyridinyl CH₂CN Et NMe₂ 3-chloro-2- N Br pyridinyl Me CH₂CN NMe₂3-chloro-2- N Br pyridinyl Et CH₂CN NMe₂ 3-chloro-2- N Br pyridinylCH₂CN CH₂CN NMe₂ 3-chloro-2- N Br pyridinyl CH₂CH₂OMe H NMe₂ 3-chloro-2-N Br pyridinyl H CH₂CH₂OMe NMe₂ 3-chloro-2- N Br pyridinyl CH₂CH₂OMeCH₂CH₂OMe NMe₂ 3-chloro-2- N Br pyridinyl CH₂CH₂SMe H NMe₂ 3-chloro-2- NBr pyridinyl H CH₂CH₂SMe NMe₂ 3-chloro-2- N Br pyridinyl Me CO₂Me NMe₂3-chloro-2- N Br pyridinyl Et CO₂Me NMe₂ 3-chloro-2- N Br pyridinyl H 2-NMe₂ 3-chloro-2- N Br pyridinyl pyridinyl H 3- NMe₂ 3-chloro-2- N Brpyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- N Br pyridinyl pyridinyl—(CH₂)₃— NMe₂ 3-chloro-2- N Br pyridinyl —(CH₂)₄— NMe₂ 3-chloro-2- N Brpyridinyl —CH₂NHCH₂— NMe₂ 3-chloro-2- N Br pyridinyl —CH₂NMeCH₂— NMe₂3-chloro-2- N Br pyridinyl —CH₂N(iso-Pr)CH₂— NMe₂ 3-chloro-2- N Brpyridinyl —CH₂N(CHO)CH₂— NMe₂ 3-chloro-2- N Br pyridinyl —CH₂N(Ac)CH₂—NMe₂ 3-chloro-2- N Br pyridinyl —CH₂N(CO₂Me)CH₂— NMe₂ 3-chloro-2- N Brpyridinyl —CH₂N(CO₂Et)CH₂— NMe₂ 3-chloro-2- N Br pyridinyl H H NMe₂3-chloro-2- N CF₃ pyridinyl Me H NMe₂ 3-chloro-2- N CF₃ pyridinyl H MeNMe₂ 3-chloro-2- N CF₃ pyridinyl Me Me NMe₂ 3-chloro-2- N CF₃ pyridinylEt H NMe₂ 3-chloro-2- N CF₃ pyridinyl H Et NMe₂ 3-chloro-2- N CF₃pyridinyl Et Et NMe₂ 3-chloro-2- N CF₃ pyridinyl n-Pr H NMe₂ 3-chloro-2-N CF₃ pyridinyl H n-Pr NMe₂ 3-chloro-2- N CF₃ pyridinyl iso-Pr H NMe₂3-chloro-2- N CF₃ pyridinyl H iso-Pr NMe₂ 3-chloro-2- N CF₃ pyridinyliso-Bu H NMe₂ 3-chloro-2- N CF₃ pyridinyl H iso-Bu NMe₂ 3-chloro-2- NCF₃ pyridinyl tert-Bu H NMe₂ 3-chloro-2- N CF₃ pyridinyl H tert-Bu NMe₂3-chloro-2- N CF₃ pyridinyl CH₂CF₃ H NMe₂ 3-chloro-2- N CF₃ pyridinyl HCH₂CF₃ NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CN H NMe₂ 3-chloro-2- N CF₃pyridinyl H CH₂CN NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂OMe H NMe₂3-chloro-2- N CF₃ pyridinyl H CH₂OMe NMe₂ 3-chloro-2- N CF₃ pyridinylCH₂CH═CH₂ H NMe₂ 3-chloro-2- N CF₃ pyridinyl H CH₂CH═CH₂ NMe₂3-chloro-2- N CF₃ pyridinyl CH₂CCH H NMe₂ 3-chloro-2- N CF₃ pyridinyl HCH₂CCH NMe₂ 3-chloro-2- N CF₃ pyridinyl H CO₂Me NMe₂ 3-chloro-2- N CF₃pyridinyl Me Et NMe₂ 3-chloro-2- N CF₃ pyridinyl Et Me NMe₂ 3-chloro-2-N CF₃ pyridinyl CH₂CH═CH₂ Me NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂Et NMe₂ 3-chloro-2- N CF₃ pyridinyl Me CH₂CH═CH₂ NMe₂ 3-chloro-2- N CF₃pyridinyl Et CH₂CH═CH₂ NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CH═CH₂CH₂CH═CH₂ NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CCH Me NMe₂ 3-chloro-2- NCF₃ pyridinyl CH₂CCH Et NMe₂ 3-chloro-2- N CF₃ pyridinyl Me CH₂CCH NMe₂3-chloro-2- N CF₃ pyridinyl Et CH₂CCH NMe₂ 3-chloro-2- N CF₃ pyridinylCH₂CCH CH₂CCH NMe₂ 3-chloro-2- N CF₃ pyridinyl cyc-Pr H NMe₂ 3-chloro-2-N CF₃ pyridinyl H cyc-Pr NMe₂ 3-chloro-2- N CF₃ pyridinyl iso-Bu iso-BuNMe₂ 3-chloro-2- N CF₃ pyridinyl sec-Bu H NMe₂ 3-chloro-2- N CF₃pyridinyl H sec-Bu NMe₂ 3-chloro-2- N CF₃ pyridinyl cyc-Bu H NMe₂3-chloro-2- N CF₃ pyridinyl H cyc-Bu NMe₂ 3-chloro-2- N CF₃ pyridinylCH₂₋cyc-Pr H NMe₂ 3-chloro-2- N CF₃ pyridinyl H CH₂₋cyc-Pr NMe₂3-chloro-2- N CF₃ pyridinyl CH₂₋cyc-Bu H NMe₂ 3-chloro-2- N CF₃pyridinyl H CH₂₋cyc-Bu NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CF3 Me NMe₂3-chloro-2- N CF₃ pyridinyl CH₂CF₃ Et NMe₂ 3-chloro-2- N CF₃ pyridinylMe CH₂CF₃ NMe₂ 3-chloro-2- N CF₃ pyridinyl Et CH₂CF₃ NMe₂ 3-chloro-2- NCF₃ pyridinyl CH₂CF₃ CH₂CF₃ NMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CN MeNMe₂ 3-chloro-2- N CF₃ pyridinyl CH₂CN Et NMe₂ 3-chloro-2- N CF₃pyridinyl Me CH₂CN NMe₂ 3-chloro-2- N CF₃ pyridinyl Et CH₂CN NMe₂3-chloro-2- N CF₃ pyridinyl CH₂CN CH₂CN NMe₂ 3-chloro-2- N CF₃ pyridinylCH₂CH₂OMe H NMe₂ 3-chloro-2- N CF₃ pyridinyl H CH₂CH₂OMe NMe₂3-chloro-2- N CF₃ pyridinyl CH₂CH₂OMe CH₂CH₂OMe NMe₂ 3-chloro-2- N CF₃pyridinyl CH₂CH₂SMe H NMe₂ 3-chloro-2- N CF₃ pyridinyl H CH₂CH₂SMe NMe₂3-chloro-2- N CF₃ pyridinyl Me CO₂Me NMe₂ 3-chloro-2- N CF₃ pyridinyl EtCO₂Me NMe₂ 3-chloro-2- N CF₃ pyridinyl H 2- NMe₂ 3-chloro-2- N CF₃pyridinyl pyridinyl H 3- NMe₂ 3-chloro-2- N CF₃ pyridinyl pyridinyl H 4-NMe₂ 3-chloro-2- N CF₃ pyridinyl pyridinyl —(CH₂)₃— NMe₂ 3-chloro-2- NCF₃ pyridinyl —(CH₂)₄— NMe₂ 3-chloro-2- N CF₃ pyridinyl —CH₂NHCH₂— NMe₂3-chloro-2- N CF₃ pyridinyl —CH₂NMeCH₂— NMe₂ 3-chloro-2- N CF₃ pyridinyl—CH₂N(iso-Pr)CH₂— NMe₂ 3-chloro-2- N CF₃ pyridinyl —CH₂N(CHO)CH₂— NMe₂3-chloro-2- N CF₃ pyridinyl —CH₂N(Ac)CH₂— NMe₂ 3-chloro-2- N CF₃pyridinyl —CH₂N(CO₂Me)CH₂— NMe₂ 3-chloro-2- N CF₃ pyridinyl—CH₂N(CO₂Et)CH₂— NMe₂ 3-chloro-2- N CF₃ pyridinyl H H SMe 3-chloro-2- NCl pyridinyl Me H SMe 3-chloro-2- N Cl pyridinyl H Me SMe 3-chloro-2- NCl pyridinyl Me Me SMe 3-chloro-2- N Cl pyridinyl Et H SMe 3-chloro-2- NCl pyridinyl H Et SMe 3-chloro-2- N Cl pyridinyl Et Et SMe 3-chloro-2- NCl pyridinyl H CO₂Me SMe 3-chloro-2- N Cl pyridinyl Me Et SMe3-chloro-2- N Cl pyridinyl Et Me SMe 3-chloro-2- N Cl pyridinylCH₂CH═CH₂ H SMe 3-chloro-2- N Cl pyridinyl H CH₂CH═CH₂ SMe 3-chloro-2- NCl pyridinyl CH₂CCH H SMe 3-chloro-2- N Cl pyridinyl H CH₂CCH SMe3-chloro-2- N Cl pyridinyl iso-Pr H SMe 3-chloro-2- N Cl pyridinyl Hiso-Pr SMe 3-chloro-2- N Cl pyridinyl H 2- SMe 3-chloro-2- N Clpyridinyl pyridinyl H 3- SMe 3-chloro-2- N Cl pyridinyl pyridinyl H 4-SMe 3-chloro-2- N Cl pyridinyl pyridinyl —(CH₂)₃— SMe 3-chloro-2- N Clpyridinyl —(CH₂)₄— SMe 3-chloro-2- N Cl pyridinyl H H SMe 3-chloro-2- NBr pyridinyl Me H SMe 3-chloro-2- N Br pyridinyl H Me SMe 3-chloro-2- NBr pyridinyl Me Me SMe 3-chloro-2- N Br pyridinyl Et H SMe 3-chloro-2- NBr pyridinyl H Et SMe 3-chloro-2- N Br pyridinyl Et Et SMe 3-chloro-2- NBr pyridinyl H CO₂Me SMe 3-chloro-2- N Br pyridinyl Me Et SMe3-chloro-2- N Br pyridinyl Et Me SMe 3-chloro-2- N Br pyridinylCH₂CH═CH₂ H SMe 3-chloro-2- N Br pyridinyl H CH₂CH═CH₂ SMe 3-chloro-2- NBr pyridinyl CH₂CCH H SMe 3-chloro-2- N Br pyridinyl H CH₂CCH SMe3-chloro-2- N Br pyridinyl iso-Pr H SMe 3-chloro-2- N Br pyridinyl Hiso-Pr SMe 3-chloro-2- N Br pyridinyl H 2- SMe 3-chloro-2- N Brpyridinyl pyridinyl H 3- SMe 3-chloro-2- N Br pyridinyl pyridinyl H 4-SMe 3-chloro-2- N Br pyridinyl pyridinyl —(CH₂)₃— SMe 3-chloro-2- N Brpyridinyl —(CH₂)₄— SMe 3-chloro-2- N Br pyridinyl H H SMe 3-chloro-2- NCF₃ pyridinyl Me H SMe 3-chloro-2- N CF₃ pyridinyl H Me SMe 3-chloro-2-N CF₃ pyridinyl Me Me SMe 3-chloro-2- N CF₃ pyridinyl Et H SMe3-chloro-2- N CF₃ pyridinyl H Et SMe 3-chloro-2- N CF₃ pyridinyl Et EtSMe 3-chloro-2- N CF₃ pyridinyl H CO₂Me SMe 3-chloro-2- N CF₃ pyridinylMe Et SMe 3-chloro-2- N CF₃ pyridinyl Et Me SMe 3-chloro-2- N CF₃pyridinyl CH₂CH═CH₂ H SMe 3-chloro-2- N CF₃ pyridinyl H CH₂CH═CH₂ SMe3-chloro-2- N CF₃ pyridinyl CH₂CCH H SMe 3-chloro-2- N CF₃ pyridinyl HCH₂CCH SMe 3-chloro-2- N CF₃ pyridinyl iso-Pr H SMe 3-chloro-2- N CF₃pyridinyl H iso-Pr SMe 3-chloro-2- N CF₃ pyridinyl H 2- SMe 3-chloro-2-N CF₃ pyridinyl pyridinyl H 3- SMe 3-chloro-2- N CF₃ pyridinyl pyridinylH 4- SMe 3-chloro-2- N CF₃ pyridinyl pyridinyl —(CH₂)₃— SMe 3-chloro-2-N CF₃ pyridinyl —(CH₂)₄— SMe 3-chloro-2- N CF₃ pyridinyl H H H3-chloro-2- CH Cl pyridinyl Me H H 3-chloro-2- CH Cl pyridinyl H Me H3-chloro-2- CH Cl pyridinyl Me Me H 3-chloro-2- CH Cl pyridinyl Et H H3-chloro-2- CH Cl pyridinyl H Et H 3-chloro-2- CH Cl pyridinyl Et Et H3-chloro-2- CH Cl pyridinyl H CO₂Me H 3-chloro-2- CH Cl pyridinyl Me EtH 3-chloro-2- CH Cl pyridinyl Et Me H 3-chloro-2- CH Cl pyridinylCH₂CH═CH₂ H H 3-chloro-2- CH Cl pyridinyl H CH₂CH═CH₂ H 3-chloro-2- CHCl pyridinyl CH₂CCH H H 3-chloro-2- CH Cl pyridinyl H CH₂CCH H3-chloro-2- CH Cl pyridinyl iso-Pr H H 3-chloro-2- CH Cl pyridinyl Hiso-Pr H 3-chloro-2- CH Cl pyridinyl H 2- H 3-chloro-2- CH Cl pyridinylpyridinyl H 3- H 3-chloro-2- CH Cl pyridinyl pyridinyl H 4- H3-chloro-2- CH Cl pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- CH Clpyridinyl —(CH₂)₄— H 3-chloro-2- CH Cl pyridinyl H H OMe 3-chloro-2- CHCl pyridinyl Me H OMe 3-chloro-2- CH Cl pyridinyl H Me OMe 3-chloro-2-CH Cl pyridinyl Me Me OMe 3-chloro-2- CH Cl pyridinyl Et H OMe3-chloro-2- CH Cl pyridinyl H Et OMe 3-chloro-2- CH Cl pyridinyl Et EtOMe 3-chloro-2- CH Cl pyridinyl H CO₂Me OMe 3-chloro-2- CH Cl pyridinylMe Et OMe 3-chloro-2- CH Cl pyridinyl Et Me OMe 3-chloro-2- CH Clpyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- CH Cl pyridinyl H CH₂CH═CH₂ OMe3-chloro-2- CH Cl pyridinyl CH₂CCH H OMe 3-chloro-2- CH Cl pyridinyl HCH₂CCH OMe 3-chloro-2- CH Cl pyridinyl iso-Pr H OMe 3-chloro-2- CH Clpyridinyl H iso-Pr OMe 3-chloro-2- CH Cl pyridinyl H 2- OMe 3-chloro-2-CH Cl pyridinyl pyridinyl H 3- OMe 3-chloro-2- CH Cl pyridinyl pyridinylH 4- OMe 3-chloro-2- CH Cl pyridinyl pyridinyl —(CH₂)₃— OMe 3-chloro-2-CH Cl pyridinyl —(CH₂)₄— OMe 3-chloro-2- CH Cl pyridinyl H H NMe₂3-chloro-2- CH Cl pyridinyl Me H NMe₂ 3-chloro-2- CH Cl pyridinyl H MeNMe₂ 3-chloro-2- CH Cl pyridinyl Me Me NMe₂ 3-chloro-2- CH Cl pyridinylEt H NMe₂ 3-chloro-2- CH Cl pyridinyl H Et NMe₂ 3-chloro-2- CH Clpyridinyl Et Et NMe₂ 3-chloro-2- CH Cl pyridinyl H CO₂Me NMe₂3-chloro-2- CH Cl pyridinyl Me Et NMe₂ 3-chloro-2- CH Cl pyridinyl Et MeNMe₂ 3-chloro-2- CH Cl pyridinyl CH₂CH═CH₂ H NMe₂ 3-chloro-2- CH Clpyridinyl H CH₂CH═CH₂ NMe₂ 3-chloro-2- CH Cl pyridinyl CH₂CCH H NMe₂3-chloro-2- CH Cl pyridinyl H CH₂CCH NMe₂ 3-chloro-2- CH Cl pyridinyliso-Pr H NMe₂ 3-chloro-2- CH Cl pyridinyl H iso-Pr NMe₂ 3-chloro-2- CHCl pyridinyl H 2- NMe₂ 3-chloro-2- CH Cl pyridinyl pyridinyl H 3- NMe₂3-chloro-2- CH Cl pyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- CH Clpyridinyl pyridinyl —(CH₂)₃— NMe₂ 3-chloro-2- CH Cl pyridinyl —(CH₂)₄—NMe₂ 3-chloro-2- CH Cl pyridinyl H H NHMe 3-chloro-2- CH Cl pyridinyl MeH NHMe 3-chloro-2- CH Cl pyridinyl H Me NHMe 3-chloro-2- CH Cl pyridinylMe Me NHMe 3-chloro-2- CH Cl pyridinyl Et H NHMe 3-chloro-2- CH Clpyridinyl H Et NHMe 3-chloro-2- CH Cl pyridinyl Et Et NHMe 3-chloro-2-CH Cl pyridinyl H CO₂Me NHMe 3-chloro-2- CH Cl pyridinyl Me Et NHMe3-chloro-2- CH Cl pyridinyl Et Me NHMe 3-chloro-2- CH Cl pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- CH Cl pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- CH Cl pyridinyl CH₂CCH H NHMe 3-chloro-2- CH Cl pyridinyl HCH₂CCH NHMe 3-chloro-2- CH Cl pyridinyl iso-Pr H NHMe 3-chloro-2- CH Clpyridinyl H iso-Pr NHMe 3-chloro-2- CH Cl pyridinyl H 2- NHMe3-chloro-2- CH Cl pyridinyl pyridinyl H 3- NHMe 3-chloro-2- CH Clpyridinyl pyridinyl H 4- NHMe 3-chloro-2- CH Cl pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- CH Cl pyridinyl —(CH₂)₄— NHMe 3-chloro-2- CHCl pyridinyl H H H 3-chloro-2- CCl H pyridinyl Me H H 3-chloro-2- CCl Hpyridinyl H Me H 3-chloro-2- CCl H pyridinyl Me Me H 3-chloro-2- CCl Hpyridinyl Et H H 3-chloro-2- CCl H pyridinyl H Et H 3-chloro-2- CCl Hpyridinyl Et Et H 3-chloro-2- CCl H pyridinyl H CO₂Me H 3-chloro-2- CClH pyridinyl Me Et H 3-chloro-2- CCl H pyridinyl Et Me H 3-chloro-2- CClH pyridinyl CH₂CH═CH₂ H H 3-chloro-2- CCl H pyridinyl H CH₂CH═CH₂ H3-chloro-2- CCl H pyridinyl CH₂CCH H H 3-chloro-2- CCl H pyridinyl HCH₂CCH H 3-chloro-2- CCl H pyridinyl iso-Pr H H 3-chloro-2- CCl Hpyridinyl H iso-Pr H 3-chloro-2- CCl H pyridinyl H 2- H 3-chloro-2- CClH pyridinyl pyridinyl H 3- H 3-chloro-2- CCl H pyridinyl pyridinyl H 4-H 3-chloro-2- CCl H pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- CCl Hpyridinyl —(CH₂)₄— H 3-chloro-2- CCl H pyridinyl H H OMe 3-chloro-2- CClH pyridinyl Me H OMe 3-chloro-2- CCl H pyridinyl H Me OMe 3-chloro-2-CCl H pyridinyl Me Me OMe 3-chloro-2- CCl H pyridinyl Et H OMe3-chloro-2- CCl H pyridinyl H Et OMe 3-chloro-2- CCl H pyridinyl Et EtOMe 3-chloro-2- CCl H pyridinyl H CO₂Me OMe 3-chloro-2- CCl H pyridinylMe Et OMe 3-chloro-2- CCl H pyridinyl Et Me OMe 3-chloro-2- CCl Hpyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- CCl H pyridinyl H CH₂CH═CH₂ OMe3-chloro-2- CCl H pyridinyl CH₂CCH H OMe 3-chloro-2- CCl H pyridinyl HCH₂CCH OMe 3-chloro-2- CCl H pyridinyl iso-Pr H OMe 3-chloro-2- CCl Hpyridinyl H iso-Pr OMe 3-chloro-2- CCl H pyridinyl H 2- OMe 3-chloro-2-CCl H pyridinyl pyridinyl H 3- OMe 3-chloro-2- CCl H pyridinyl pyridinylH 4- OMe 3-chloro-2- CCl H pyridinyl pyridinyl —(CH₂)₃— OMe 3-chloro-2-CCl H pyridinyl —(CH₂)₄— OMe 3-chloro-2- CCl H pyridinyl H H NMe₂3-chloro-2- CCl H pyridinyl Me H NMe₂ 3-chloro-2- CCl H pyridinyl H MeNMe₂ 3-chloro-2- CCl H pyridinyl Me Me NMe₂ 3-chloro-2- CCl H pyridinylEt H NMe₂ 3-chloro-2- CCl H pyridinyl H Et NMe₂ 3-chloro-2- CCl Hpyridinyl Et Et NMe₂ 3-chloro-2- CCl H pyridinyl H CO₂Me NMe₂3-chloro-2- CCl H pyridinyl Me Et NMe₂ 3-chloro-2- CCl H pyridinyl Et MeNMe₂ 3-chloro-2- CCl H pyridinyl CH₂CH═CH₂ H NMe₂ 3-chloro-2- CCl Hpyridinyl H CH₂CH═CH₂ NMe₂ 3-chloro-2- CCl H pyridinyl CH₂CCH H NMe₂3-chloro-2- CCl H pyridinyl H CH₂CCH NMe₂ 3-chloro-2- CCl H pyridinyliso-Pr H NMe₂ 3-chloro-2- CCl H pyridinyl H iso-Pr NMe₂ 3-chloro-2- CClH pyridinyl H 2- NMe₂ 3-chloro-2- CCl H pyridinyl pyridinyl H 3- NMe₂3-chloro-2- CCl H pyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- CCl Hpyridinyl pyridinyl —(CH₂)₃— NMe₂ 3-chloro-2- CCl H pyridinyl —(CH₂)₄—NMe₂ 3-chloro-2- CCl H pyridinyl H H NHMe 3-chloro-2- CCl H pyridinyl MeH NHMe 3-chloro-2- CC H pyridinyl H Me NHMe 3-chloro-2- CCl H pyridinylMe Me NHMe 3-chloro-2- CCl H pyridinyl Et H NHMe 3-chloro-2- CCl Hpyridinyl H Et NHMe 3-chloro-2- CCl H pyridinyl Et Et NHMe 3-chloro-2-CCl H pyridinyl H CO₂Me NHMe 3-chloro-2- CCl H pyridinyl Me Et NHMe3-chloro-2- CCl H pyridinyl Et Me NHMe 3-chloro-2- CCl H pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- CCl H pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- CCl H pyridinyl CH₂CCH H NHMe 3-chloro-2- CCl H pyridinyl HCH₂CCH NHMe 3-chloro-2- CCl H pyridinyl iso-Pr H NHMe 3-chloro-2- CCl Hpyridinyl H iso-Pr NHMe 3-chloro-2- CCl H pyridinyl H 2- NHMe3-chloro-2- CCl H pyridinyl pyridinyl H 3- NHMe 3-chloro-2- CCl Hpyridinyl pyridinyl H 4- NHMe 3-chloro-2- CCl H pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- CCl H pyridinyl —(CH₂)₄— NHMe 3-chloro-2- CClH pyridinyl H H H 3-chloro-2- CCl Cl pyridinyl Me H H 3-chloro-2- CCl Clpyridinyl H Me H 3-chloro-2- CCl Cl pyridinyl Me Me H 3-chloro-2- CCl Clpyridinyl Et H H 3-chloro-2- CCl Cl pyridinyl H Et H 3-chloro-2- CCl Clpyridinyl Et Et H 3-chloro-2- CCl Cl pyridinyl H CO₂Me H 3-chloro-2- CClCl pyridinyl Me Et H 3-chloro-2- CCl Cl pyridinyl Et Me H 3-chloro-2-CCl Cl pyridinyl CH₂CH═CH₂ H H 3-chloro-2- CCl Cl pyridinyl H CH₂CH═CH₂H 3-chloro-2- CCl Cl pyridinyl CH₂CCH H H 3-chloro-2- CCl Cl pyridinyl HCH₂CCH H 3-chloro-2- CCl Cl pyridinyl iso-Pr H H 3-chloro-2- CCl Clpyridinyl H iso-Pr H 3-chloro-2- CCl Cl pyridinyl H 2- H 3-chloro-2- CClCl pyridinyl pyridinyl H 3- H 3-chloro-2- CCl Cl pyridinyl pyridinyl H4- H 3-chloro-2- CCl Cl pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- CClCl pyridinyl —(CH₂)₄— H 3-chloro-2- CCl Cl pyridinyl H H OMe 3-chloro-2-CCl Cl pyridinyl Me H OMe 3-chloro-2- CCl Cl pyridinyl H Me OMe3-chloro-2- CCl Cl pyridinyl Me Me OMe 3-chloro-2- CCl Cl pyridinyl Et HOMe 3-chloro-2- CCl Cl pyridinyl H Et OMe 3-chloro-2- CCl Cl pyridinylEt Et OMe 3-chloro-2- CCl Cl pyridinyl H CO₂Me OMe 3-chloro-2- CCl Clpyridinyl Me Et OMe 3-chloro-2- CCl Cl pyridinyl Et Me OMe 3-chloro-2-CCl Cl pyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- CCl Cl pyridinyl HCH₂CH═CH₂ OMe 3-chloro-2- CCl Cl pyridinyl CH₂CCH H OMe 3-chloro-2- CClCl pyridinyl H CH₂CCH OMe 3-chloro-2- CCl Cl pyridinyl iso-Pr H OMe3-chloro-2- CCl Cl pyridinyl H iso-Pr OMe 3-chloro-2- CCl Cl pyridinyl H2- OMe 3-chloro-2- CCl Cl pyridinyl pyridinyl H 3- OMe 3-chloro-2- CClCl pyridinyl pyridinyl H 4- OMe 3-chloro-2- CCl Cl pyridinyl pyridinyl—(CH₂)₃— OMe 3-chloro-2- CCl Cl pyridinyl —(CH₂)₄— OMe 3-chloro-2- CClCl pyridinyl H H NMe₂ 3-chloro-2- CCl Cl pyridinyl Me H NMe₂ 3-chloro-2-CCl Cl pyridinyl H Me NMe₂ 3-chloro-2- CCl Cl pyridinyl Me Me NMe₂3-chloro-2- CCl Cl pyridinyl Et H NMe₂ 3-chloro-2- CCl Cl pyridinyl H EtNMe₂ 3-chloro-2- CCl Cl pyridinyl Et Et NMe₂ 3-chloro-2- CCl Clpyridinyl H CO₂Me NMe₂ 3-chloro-2- CCl Cl pyridinyl Me Et NMe₂3-chloro-2- CCl Cl pyridinyl Et Me NMe₂ 3-chloro-2- CCl Cl pyridinylCH₂CH═CH₂ H NMe₂ 3-chloro-2- CCl Cl pyridinyl H CH₂CH═CH₂ NMe₂3-chloro-2- CCl Cl pyridinyl CH₂CCH H NMe₂ 3-chloro-2- CCl Cl pyridinylH CH₂CCH NMe₂ 3-chloro-2- CCl Cl pyridinyl iso-Pr H NMe₂ 3-chloro-2- CClCl pyridinyl H iso-Pr NMe₂ 3-chloro-2- CCl Cl pyridinyl H 2- NMe₂3-chloro-2- CCl Cl pyridinyl pyridinyl H 3- NMe₂ 3-chloro-2- CCl Clpyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- CCl Cl pyridinyl pyridinyl—(CH₂)₃— NMe₂ 3-chloro-2- CCl Cl pyridinyl —(CH₂)₄— NMe₂ 3-chloro-2- CClCl pyridinyl H H NHMe 3-chloro-2- CCl Cl pyridinyl Me H NHMe 3-chloro-2-CCl Cl pyridinyl H Me NHMe 3-chloro-2- CCl Cl pyridinyl Me Me NHMe3-chloro-2- CCl Cl pyridinyl Et H NHMe 3-chloro-2- CCl Cl pyridinyl H EtNHMe 3-chloro-2- CCl Cl pyridinyl Et Et NHMe 3-chloro-2- CCl Clpyridinyl H CO₂Me NHMe 3-chloro-2- CCl Cl pyridinyl Me Et NHMe3-chloro-2- CCl Cl pyridinyl Et Me NHMe 3-chloro-2- CCl Cl pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- CCl Cl pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- CCl Cl pyridinyl CH₂CCH H NHMe 3-chloro-2- CCl Cl pyridinylH CH₂CCH NHMe 3-chloro-2- CCl Cl pyridinyl iso-Pr H NHMe 3-chloro-2- CClCl pyridinyl H iso-Pr NHMe 3-chloro-2- CCl Cl pyridinyl H 2- NHMe3-chloro-2- CCl Cl pyridinyl pyridinyl H 3- NHMe 3-chloro-2- CCl Clpyridinyl pyridinyl H 4- NHMe 3-chloro-2- CCl Cl pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- CCl Cl pyridinyl —(CH₂)₄— NHMe 3-chloro-2- CClCl pyridinyl H H H 3-chloro-2- CH Br pyridinyl Me H H 3-chloro-2- CH Brpyridinyl H Me H 3-chloro-2- CH Br pyridinyl Me Me H 3-chloro-2- CH Brpyridinyl Et H H 3-chloro-2- CH Br pyridinyl H Et H 3-chloro-2- CH Brpyridinyl Et Et H 3-chloro-2- CH Br pyridinyl H CO₂Me H 3-chloro-2- CHBr pyridinyl Me Et H 3-chloro-2- CH Br pyridinyl Et Me H 3-chloro-2- CHBr pyridinyl CH₂CH═CH₂ H H 3-chloro-2- CH Br pyridinyl H CH₂CH═CH₂ H3-chloro-2- CH Br pyridinyl CH₂CCH H H 3-chloro-2- CH Br pyridinyl HCH₂CCH H 3-chloro-2- CH Br pyridinyl iso-Pr H H 3-chloro-2- CH Brpyridinyl H iso-Pr H 3-chloro-2- CH Br pyridinyl H 2- H 3-chloro-2- CHBr pyridinyl pyridinyl H 3- H 3-chloro-2- CH Br pyridinyl pyridinyl H 4-H 3-chloro-2- CH Br pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- CH Brpyridinyl —(CH₂)₄— H 3-chloro-2- CH Br pyridinyl H H OMe 3-chloro-2- CHBr pyridinyl Me H OMe 3-chloro-2- CH Br pyridinyl H Me OMe 3-chloro-2-CH Br pyridinyl Me Me OMe 3-chloro-2- CH Br pyridinyl Et H OMe3-chloro-2- CH Br pyridinyl H Et OMe 3-chloro-2- CH Br pyridinyl Et EtOMe 3-chloro-2- CH Br pyridinyl H CO₂Me OMe 3-chloro-2- CH Br pyridinylMe Et OMe 3-chloro-2- CH Br pyridinyl Et Me OMe 3-chloro-2- CH Brpyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- CH Br pyridinyl H CH₂CH═CH₂ OMe3-chloro-2- CH Br pyridinyl CH₂CCH H OMe 3-chloro-2- CH Br pyridinyl HCH₂CCH OMe 3-chloro-2- CH Br pyridinyl iso-Pr H OMe 3-chloro-2- CH Brpyridinyl H iso-Pr OMe 3-chloro-2- CH Br pyridinyl H 2- OMe 3-chloro-2-CH Br pyridinyl pyridinyl H 3- OMe 3-chloro-2- CH Br pyridinyl pyridinylH 4- OMe 3-chloro-2- CH Br pyridinyl pyridinyl —(CH₂)₃— OMe 3-chloro-2-CH Br pyridinyl —(CH₂)₄— OMe 3-chloro-2- CH Br pyridinyl H H NMe₂3-chloro-2- CH Br pyridinyl Me H NMe₂ 3-chloro-2- CH Br pyridinyl H MeNMe₂ 3-chloro-2- CH Br pyridinyl Me Me NMe₂ 3-chloro-2- CH Br pyridinylEt H NMe₂ 3-chloro-2- CH Br pyridinyl H Et NMe₂ 3-chloro-2- CH Brpyridinyl Et Et NMe₂ 3-chloro-2- CH Br pyridinyl H CO₂Me NMe₂3-chloro-2- CH Br pyridinyl Me Et NMe₂ 3-chloro-2- CH Br pyridinyl Et MeNMe₂ 3-chloro-2- CH Br pyridinyl CH₂CH═CH₂ H NMe₂ 3-chloro-2- CH Brpyridinyl H CH₂CH═CH₂ NMe₂ 3-chloro-2- CH Br pyridinyl CH₂CCH H NMe₂3-chloro-2- CH Br pyridinyl H CH₂CCH NMe₂ 3-chloro-2- CH Br pyridinyliso-Pr H NMe₂ 3-chloro-2- CH Br pyridinyl H iso-Pr NMe₂ 3-chloro-2- CHBr pyridinyl H 2- NMe₂ 3-chloro-2- CH Br pyridinyl pyridinyl H 3- NMe₂3-chloro-2- CH Br pyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- CH Brpyridinyl pyridinyl —(CH₂)₃— NMe₂ 3-chloro-2- CH Br pyridinyl —(CH₂)₄—NMe₂ 3-chloro-2- CH Br pyridinyl H H NHMe 3-chloro-2- CH Br pyridinyl MeH NHMe 3-chloro-2- CH Br pyridinyl H Me NHMe 3-chloro-2- CH Br pyridinylMe Me NHMe 3-chloro-2- CH Br pyridinyl Et H NHMe 3-chloro-2- CH Brpyridinyl H Et NHMe 3-chloro-2- CH Br pyridinyl Et Et NHMe 3-chloro-2-CH Br pyridinyl H CO₂Me NHMe 3-chloro-2- CH Br pyridinyl Me Et NHMe3-chloro-2- CH Br pyridinyl Et Me NHMe 3-chloro-2- CH Br pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- CH Br pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- CH Br pyridinyl CH₂CCH H NHMe 3-chloro-2- CH Br pyridinyl HCH₂CCH NHMe 3-chloro-2- CH Br pyridinyl iso-Pr H NHMe 3-chloro-2- CH Brpyridinyl H iso-Pr NHMe 3-chloro-2- CH Br pyridinyl H 2- NHMe3-chloro-2- CH Br pyridinyl pyridinyl H 3- NHMe 3-chloro-2- CH Brpyridinyl pyridinyl H 4- NHMe 3-chloro-2- CH Br pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- CH Br pyridinyl —(CH₂)₄— NHMe 3-chloro-2- CHBr pyridinyl H H H 3-chloro-2- CBr H pyridinyl Me H H 3-chloro-2- CBr Hpyridinyl H Me H 3-chloro-2- CBr H pyridinyl Me Me H 3-chloro-2- CBr Hpyridinyl Et H H 3-chloro-2- CBr H pyridinyl H Et H 3-chloro-2- CBr Hpyridinyl Et Et H 3-chloro-2- CBr H pyridinyl H CO₂Me H 3-chloro-2- CBrH pyridinyl Me Et H 3-chloro-2- CBr H pyridinyl Et Me H 3-chloro-2- CBrH pyridinyl CH₂CH═CH₂ H H 3-chloro-2- CBr H pyridinyl H CH₂CH═CH₂ H3-chloro-2- CBr H pyridinyl CH₂CCH H H 3-chloro-2- CBr H pyridinyl HCH₂CCH H 3-chloro-2- CBr H pyridinyl iso-Pr H H 3-chloro-2- CBr Hpyridinyl H iso-Pr H 3-chloro-2- CBr H pyridinyl H 2- H 3-chloro-2- CBrH pyridinyl pyridinyl H 3- H 3-chloro-2- CBr H pyridinyl pyridinyl H 4-H 3-chloro-2- CBr H pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- CBr Hpyridinyl —(CH₂)₄— H 3-chloro-2- CBr H pyridinyl H H OMe 3-chloro-2- CBrH pyridinyl Me H OMe 3-chloro-2- CBr H pyridinyl H Me OMe 3-chloro-2-CBr H pyridinyl Me Me OMe 3-chloro-2- CBr H pyridinyl Et H OMe3-chloro-2- CBr H pyridinyl H Et OMe 3-chloro-2- CBr H pyridinyl Et EtOMe 3-chloro-2- CBr H pyridinyl H CO₂Me OMe 3-chloro-2- CBr H pyridinylMe Et OMe 3-chloro-2- CBr H pyridinyl Et Me OMe 3-chloro-2- CBr Hpyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- CBr H pyridinyl H CH₂CH═CH₂ OMe3-chloro-2- CBr H pyridinyl CH₂CCH H OMe 3-chloro-2- CBr H pyridinyl HCH₂CCH OMe 3-chloro-2- CBr H pyridinyl iso-Pr H OMe 3-chloro-2- CBr Hpyridinyl H iso-Pr OMe 3-chloro-2- CBr H pyridinyl H 2- OMe 3-chloro-2-CBr H pyridinyl pyridinyl H 3- OMe 3-chloro-2- CBr H pyridinyl pyridinylH 4- OMe 3-chloro-2- CBr H pyridinyl pyridinyl —(CH₂)₃— OMe 3-chloro-2-CBr H pyridinyl —(CH₂)₄— OMe 3-chloro-2- CBr H pyridinyl H H NMe₂3-chloro-2- CBr H pyridinyl Me H NMe₂ 3-chloro-2- CBr H pyridinyl H MeNMe₂ 3-chloro-2- CBr H pyridinyl Me Me NMe₂ 3-chloro-2- CBr H pyridinylEt H NMe₂ 3-chloro-2- CBr H pyridinyl H Et NMe₂ 3-chloro-2- CBr Hpyridinyl Et Et NMe₂ 3-chloro-2- CBr H pyridinyl H CO₂Me NMe₂3-chloro-2- CBr H pyridinyl Me Et NMe₂ 3-chloro-2- CBr H pyridinyl Et MeNMe₂ 3-chloro-2- CBr H pyridinyl CH₂CH═CH₂ H NMe₂ 3-chloro-2- CBr Hpyridinyl H CH₂CH═CH₂ NMe₂ 3-chloro-2- CBr H pyridinyl CH₂CCH H NMe₂3-chloro-2- CBr H pyridinyl H CH₂CCH NMe₂ 3-chloro-2- CBr H pyridinyliso-Pr H NMe₂ 3-chloro-2- CBr H pyridinyl H iso-Pr NMe₂ 3-chloro-2- CBrH pyridinyl H 2- NMe₂ 3-chloro-2- CBr H pyridinyl pyridinyl H 3- NMe₂3-chloro-2- CBr H pyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- CBr Hpyridinyl pyridinyl —(CH₂)₃— NMe₂ 3-chloro-2- CBr H pyridinyl —(CH₂)₄—NMe₂ 3-chloro-2- CBr H pyridinyl H H NHMe 3-chloro-2- CBr H pyridinyl MeH NHMe 3-chloro-2- CBr H pyridinyl H Me NHMe 3-chloro-2- CBr H pyridinylMe Me NHMe 3-chloro-2- CBr H pyridinyl Et H NHMe 3-chloro-2- CBr Hpyridinyl H Et NHMe 3-chloro-2- CBr H pyridinyl Et Et NHMe 3-chloro-2-CBr H pyridinyl H CO₂Me NHMe 3-chloro-2- CBr H pyridinyl Me Et NHMe3-chloro-2- CBr H pyridinyl Et Me NHMe 3-chloro-2- CBr H pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- CBr H pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- CBr H pyridinyl CH₂CCH H NHMe 3-chloro-2- CBr H pyridinyl HCH₂CCH NHMe 3-chloro-2- CBr H pyridinyl iso-Pr H NHMe 3-chloro-2- CBr Hpyridinyl H iso-Pr NHMe 3-chloro-2- CBr H pyridinyl H 2- NHMe3-chloro-2- CBr H pyridinyl pyridinyl H 3- NHMe 3-chloro-2- CBr Hpyridinyl pyridinyl H 4- NHMe 3-chloro-2- CBr H pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- PCBr H pyridinyl —(CH₂)₄— NHMe 3-chloro-2- CBrH pyridinyl H H H 3-chloro-2- CBr Br pyridinyl Me H H 3-chloro-2- CBr Brpyridinyl H Me H 3-chloro-2- CBr Br pyridinyl Me Me H 3-chloro-2- CBr Brpyridinyl Et H H 3-chloro-2- CBr Br pyridinyl H Et H 3-chloro-2- CBr Brpyridinyl Et Et H 3-chloro-2- CBr Br pyridinyl H CO₂Me H 3-chloro-2- CBrBr pyridinyl Me Et H 3-chloro-2- CBr Br pyridinyl Et Me H 3-chloro-2-CBr Br pyridinyl CH₂CH═CH₂ H H 3-chloro-2- CBr Br pyridinyl H CH₂CH═CH₂H 3-chloro-2- CBr Br pyridinyl CH₂CCH H H 3-chloro-2- CBr Br pyridinyl HCH₂CCH H 3-chloro-2- CBr Br pyridinyl iso-Pr H H 3-chloro-2- CBr Brpyridinyl H iso-Pr H 3-chloro-2- CBr Br pyridinyl H 2- H 3-chloro-2- CBrBr pyridinyl pyridinyl H 3- H 3-chloro-2- CBr Br pyridinyl pyridinyl H4- H 3-chloro-2- CBr Br pyridinyl pyridinyl —(CH₂)₃— H 3-chloro-2- CBrBr pyridinyl —(CH₂)₄— H 3-chloro-2- CBr Br pyridinyl H H OMe 3-chloro-2-CBr Br pyridinyl Me H OMe 3-chloro-2- CBr Br pyridinyl H Me OMe3-chloro-2- CBr Br pyridinyl Me Me OMe 3-chloro-2- CBr Br pyridinyl Et HOMe 3-chloro-2- CBr Br pyridinyl H Et OMe 3-chloro-2- CBr Br pyridinylEt Et OMe 3-chloro-2- CBr Br pyridinyl H CO₂Me OMe 3-chloro-2- CBr Brpyridinyl Me Et OMe 3-chloro-2- CBr Br pyridinyl Et Me OMe 3-chloro-2-CBr Br pyridinyl CH₂CH═CH₂ H OMe 3-chloro-2- CBr Br pyridinyl HCH₂CH═CH₂ OMe 3-chloro-2- CBr Br pyridinyl CH₂CCH H OMe 3-chloro-2- CBrBr pyridinyl H CH₂CCH OMe 3-chloro-2- CBr Br pyridinyl iso-Pr H OMe3-chloro-2- CBr Br pyridinyl H iso-Pr OMe 3-chloro-2- CBr Br pyridinyl H2- OMe 3-chloro-2- CBr Br pyridinyl pyridinyl H 3- OMe 3-chloro-2- CBrBr pyridinyl pyridinyl H 4- OMe 3-chloro-2- CBr Br pyridinyl pyridinyl—(CH₂)₃— OMe 3-chloro-2- CBr Br pyridinyl —(CH₂)₄— OMe 3-chloro-2- CBrBr pyridinyl H H NMe₂ 3-chloro-2- CBr Br pyridinyl Me H NMe₂ 3-chloro-2-CBr Br pyridinyl H Me NMe₂ 3-chloro-2- CBr Br pyridinyl Me Me NMe₂3-chloro-2- CBr Br pyridinyl Et H NMe₂ 3-chloro-2- CBr Br pyridinyl H EtNMe₂ 3-chloro-2- CBr Br pyridinyl Et Et NMe₂ 3-chloro-2- CBr Brpyridinyl H CO₂Me NMe₂ 3-chloro-2- CBr Br pyridinyl Me Et NMe₂3-chloro-2- CBr Br pyridinyl Et Me NMe₂ 3-chloro-2- CBr Br pyridinylCH₂CH═CH₂ H NMe₂ 3-chloro-2- CBr Br pyridinyl H CH₂CH═CH₂ NMe₂3-chloro-2- CBr Br pyridinyl CH₂CCH H NMe₂ 3-chloro-2- CBr Br pyridinylH CH₂CCH NMe₂ 3-chloro-2- CBr Br pyridinyl iso-Pr H NMe₂ 3-chloro-2- CBrBr pyridinyl H iso-Pr NMe₂ 3-chloro-2- CBr Br pyridinyl H 2- NMe₂3-chloro-2- CBr Br pyridinyl pyridinyl H 3- NMe₂ 3-chloro-2- CBr Brpyridinyl pyridinyl H 4- NMe₂ 3-chloro-2- CBr Br pyridinyl pyridinyl—(CH₂)₃— NMe₂ 3-chloro-2- CBr Br pyridinyl —(CH₂)₄— NMe₂ 3-chloro-2- CBrBr pyridinyl H H NHMe 3-chloro-2- CBr Br pyridinyl Me H NHMe 3-chloro-2-CBr Br pyridinyl H Me NHMe 3-chloro-2- CBr Br pyridinyl Me Me NHMe3-chloro-2- CBr Br pyridinyl Et H NHMe 3-chloro-2- CBr Br pyridinyl H EtNHMe 3-chloro-2- CBr Br pyridinyl Et Et NHMe 3-chloro-2- CBr Brpyridinyl H CO₂Me NHMe 3-chloro-2- CBr Br pyridinyl Me Et NHMe3-chloro-2- CBr Br pyridinyl Et Me NHMe 3-chloro-2- CBr Br pyridinylCH₂CH═CH₂ H NHMe 3-chloro-2- CBr Br pyridinyl H CH₂CH═CH₂ NHMe3-chloro-2- CBr Br pyridinyl CH₂CCH H NHMe 3-chloro-2- CBr Br pyridinylH CH₂CCH NHMe 3-chloro-2- CBr Br pyridinyl iso-Pr H NHMe 3-chloro-2- CBrBr pyridinyl H iso-Pr NHMe 3-chloro-2- CBr Br pyridinyl H 2- NHMe3-chloro-2- CBr Br pyridinyl pyridinyl H 3- NHMe 3-chloro-2- CBr Brpyridinyl pyridinyl H 4- NHMe 3-chloro-2- CBr Br pyridinyl pyridinyl—(CH₂)₃— NHMe 3-chloro-2- CBr Br pyridinyl —(CH₂)₄— NHMe 3-chloro-2- CBrBr pyridinyl H H H 2-chlorophenyl N Cl Me H H 2-chlorophenyl N Cl H Me H2-chlorophenyl N Cl Me Me H 2-chlorophenyl N Cl Et H H 2-chlorophenyl NCl H Et H 2-chlorophenyl N Cl Et Et H 2-chlorophenyl N Cl H CO₂Me H2-chlorophenyl N Cl Me Et H 2-chlorophenyl N Cl Et Me H 2-chlorophenyl NCl CH₂CH═CH₂ H H 2-chlorophenyl N Cl H CH₂CH═CH₂ H 2-chlorophenyl N ClCH₂CCH H H 2-chlorophenyl N Cl H CH₂CCH H 2-chlorophenyl N Cl iso-Pr H H2-chlorophenyl N Cl H iso-Pr H 2-chlorophenyl N Cl H 2- H 2-chlorophenylN Cl pyridinyl H 3- H 2-chlorophenyl N Cl pyridinyl H 4- H2-chlorophenyl N Cl pyridinyl —(CH₂)₃— H 2-chlorophenyl N Cl —(CH₂)₄— H2-chlorophenyl N Cl H H H 2-chlorophenyl N Br Me H H 2-chlorophenyl N BrH Me H 2-chlorophenyl N Br Me Me H 2-chlorophenyl N Br Et H H2-chlorophenyl N Br H Et H 2-chlorophenyl N Br Et Et H 2-chlorophenyl NBr H CO₂Me H 2-chlorophenyl N Br Me Et H 2-chlorophenyl N Br Et Me H2-chlorophenyl N Br CH₂CH═CH₂ H H 2-chlorophenyl N Br H CH₂CH═CH₂ H2-chlorophenyl N Br CH₂CCH H H 2-chlorophenyl N Br H CH₂CCH H2-chlorophenyl N Br iso-Pr H H 2-chlorophenyl N Br H iso-Pr H2-chlorophenyl N Br H 2- H 2-chlorophenyl N Br pyridinyl H 3- H2-chlorophenyl N Br pyridinyl H 4- H 2-chlorophenyl N Br pyridinyl—(CH₂)₃— H 2-chlorophenyl N Br —(CH₂)₄— H 2-chlorophenyl N Br H H H2-chlorophenyl N CF₃ Me H H 2-chlorophenyl N CF₃ H Me H 2-chlorophenyl NCF₃ Me Me H 2-chlorophenyl N CF₃ Et H H 2-chlorophenyl N CF₃ H Et H2-chlorophenyl N CF₃ Et Et H 2-chlorophenyl N CF₃ H CO₂Me H2-chlorophenyl N CF₃ Me Et H 2-chlorophenyl N CF₃ Et Me H 2-chlorophenylN CF₃ CH₂CH═CH₂ H H 2-chlorophenyl N CF₃ H CH₂CH═CH₂ H 2-chlorophenyl NCF₃ CH₂CCH H H 2-chlorophenyl N CF₃ H CH₂CCH H 2-chlorophenyl N CF₃iso-Pr H H 2-chlorophenyl N CF₃ H iso-Pr H 2-chlorophenyl N CF₃ H 2- H2-chlorophenyl N CF₃ pyridinyl H 3- H 2-chlorophenyl N CF₃ pyridinyl H4- H 2-chlorophenyl N CF₃ pyridinyl —(CH₂)₃— H 2-chlorophenyl N CF₃—(CH₂)₄— H 2-chlorophenyl N CF₃ H H OMe 2-chlorophenyl N Cl Me H OMe2-chlorophenyl N Cl H Me OMe 2-chlorophenyl N Cl Me Me OMe2-chlorophenyl N Cl Et H OMe 2-chlorophenyl N Cl H Et OMe 2-chlorophenylN Cl Et Et OMe 2-chlorophenyl N Cl H CO₂Me OMe 2-chlorophenyl N Cl Me EtOMe 2-chlorophenyl N Cl Et Me OMe 2-chlorophenyl N Cl CH₂CH═CH₂ H OMe2-chlorophenyl N Cl H CH₂CH═CH₂ OMe 2-chlorophenyl N Cl CH₂CCH H OMe2-chlorophenyl N Cl H CH₂CCH OMe 2-chlorophenyl N Cl iso-Pr H OMe2-chlorophenyl N Cl H iso-Pr OMe 2-chlorophenyl N Cl H 2- OMe2-chlorophenyl N Cl pyridinyl H 3- OMe 2-chlorophenyl N Cl pyridinyl H4- OMe 2-chlorophenyl N Cl pyridinyl —(CH₂)₃— OMe 2-chlorophenyl N Cl—(CH₂)₄— OMe 2-chlorophenyl N Cl H H OMe 2-chlorophenyl N Br Me H OMe2-chlorophenyl N Br H Me OMe 2-chlorophenyl N Br Me Me OMe2-chlorophenyl N Br Et H OMe 2-chlorophenyl N Br H Et OMe 2-chlorophenylN Br Et Et OMe 2-chlorophenyl N Br H CO₂Me OMe 2-chlorophenyl N Br Me EtOMe 2-chlorophenyl N Br Et Me OMe 2-chlorophenyl N Br CH₂CH═CH₂ H OMe2-chlorophenyl N Br H CH₂CH═CH₂ OMe 2-chlorophenyl N Br CH₂CCH H OMe2-chlorophenyl N Br H CH₂CCH OMe 2-chlorophenyl N Br iso-Pr H OMe2-chlorophenyl N Br H iso-Pr OMe 2-chlorophenyl N Br H 2- OMe2-chlorophenyl N Br pyridinyl H 3- OMe 2-chlorophenyl N Br pyridinyl H4- OMe 2-chlorophenyl N Br pyridinyl —(CH₂)₃— OMe 2-chlorophenyl N Br—(CH₂)₄— OMe 2-chlorophenyl N Br H H OMe 2-chlorophenyl N CF₃ Me H OMe2-chlorophenyl N CF₃ H Me OMe 2-chlorophenyl N CF₃ Me Me OMe2-chlorophenyl N CF₃ Et H OMe 2-chlorophenyl N CF₃ H Et OMe2-chlorophenyl N CF₃ Et Et OMe 2-chlorophenyl N CF₃ H CO₂Me OMe2-chlorophenyl N CF₃ Me Et OMe 2-chlorophenyl N CF₃ Et Me OMe2-chlorophenyl N CF₃ CH₂CH═CH₂ H OMe 2-chlorophenyl N CF₃ H CH₂CH═CH₂OMe 2-chlorophenyl N CF₃ CH₂CCH H OMe 2-chlorophenyl N CF₃ H CH₂CCH OMe2-chlorophenyl N CF₃ iso-Pr H OMe 2-chlorophenyl N CF₃ H iso-Pr OMe2-chlorophenyl N CF₃ H 2- OMe 2-chlorophenyl N CF₃ pyridinyl H 3- OMe2-chlorophenyl N CF₃ pyridinyl H 4- OMe 2-chlorophenyl N CF₃ pyridinyl—(CH₂)₃— OMe 2-chlorophenyl N CF₃ —(CH₂)₄— OMe 2-chlorophenyl N CF₃ H HNHMe 2-chlorophenyl N Cl Me H NHMe 2-chlorophenyl N Cl H Me NHMe2-chlorophenyl N Cl Me Me NHMe 2-chlorophenyl N Cl Et H NHMe2-chlorophenyl N Cl H Et NHMe 2-chlorophenyl N Cl Et Et NHMe2-chlorophenyl N Cl H CO₂Me NHMe 2-chlorophenyl N Cl Me Et NHMe2-chlorophenyl N Cl Et Me NHMe 2-chlorophenyl N Cl CH₂CH═CH₂ H NHMe2-chlorophenyl N Cl H CH₂CH═CH₂ NHMe 2-chlorophenyl N Cl CH₂CCH H NHMe2-chlorophenyl N Cl H CH₂CCH NHMe 2-chlorophenyl N Cl iso-Pr H NHMe2-chlorophenyl N Cl H iso-Pr NHMe 2-chlorophenyl N Cl H 2- NHMe2-chlorophenyl N Cl pyridinyl H 3- NHMe 2-chlorophenyl N Cl pyridinyl H4- NHMe 2-chlorophenyl N Cl pyridinyl —(CH₂)₃— NHMe 2-chlorophenyl N Cl—(CH₂)₄— NHMe 2-chlorophenyl N Cl H H NHMe 2-chlorophenyl N Br Me H NHMe2-chlorophenyl N Br H Me NHMe 2-chlorophenyl N Br Me Me NHMe2-chlorophenyl N Br Et H NHMe 2-chlorophenyl N Br H Et NHMe2-chlorophenyl N Br Et Et NHMe 2-chlorophenyl N Br H CO₂Me NHMe2-chlorophenyl N Br Me Et NHMe 2-chlorophenyl N Br Et Me NHMe2-chlorophenyl N Br CH₂CH═CH₂ H NHMe 2-chlorophenyl N Br H CH₂CH═CH₂NHMe 2-chlorophenyl N Br CH₂CCH H NHMe 2-chlorophenyl N Br H CH₂CCH NHMe2-chlorophenyl N Br iso-Pr H NHMe 2-chlorophenyl N Br H iso-Pr NHMe2-chlorophenyl N Br H 2- NHMe 2-chlorophenyl N Br pyridinyl H 3- NHMe2-chlorophenyl N Br pyridinyl H 4- NHMe 2-chlorophenyl N Br pyridinyl—(CH₂)₃— NHMe 2-chlorophenyl N Br —(CH₂)₄— NHMe 2-chlorophenyl N Br H HNHMe 2-chlorophenyl N CF₃ Me H NHMe 2-chlorophenyl N CF₃ H Me NHMe2-chlorophenyl N CF₃ Me Me NHMe 2-chlorophenyl N CF₃ Et H NHMe2-chlorophenyl N CF₃ H Et NHMe 2-chlorophenyl N CF₃ Et Et NHMe2-chlorophenyl N CF₃ H CO₂Me NHMe 2-chlorophenyl N CF₃ Me Et NHMe2-chlorophenyl N CF₃ Et Me NHMe 2-chlorophenyl N CF₃ CH₂CH═CH₂ H NHMe2-chlorophenyl N CF₃ H CH₂CH═CH₂ NHMe 2-chlorophenyl N CF₃ CH₂CCH H NHMe2-chlorophenyl N CF₃ H CH₂CCH NHMe 2-chlorophenyl N CF₃ iso-Pr H NHMe2-chlorophenyl N CF₃ H iso-Pr NHMe 2-chlorophenyl N CF₃ H 2- NHMe2-chlorophenyl N CF₃ pyridinyl H 3- NHMe 2-chlorophenyl N CF₃ pyridinylH 4- NHMe 2-chlorophenyl N CF₃ pyridinyl —(CH₂)₃— NHMe 2-chlorophenyl NCF₃ —(CH₂)₄— NHMe 2-chlorophenyl N CF₃ H H NMe₂ 2-chlorophenyl N Cl Me HNMe₂ 2-chlorophenyl N Cl H Me NMe₂ 2-chlorophenyl N Cl Me Me NMe₂2-chlorophenyl N Cl Et H NMe₂ 2-chlorophenyl N Cl H Et NMe₂2-chlorophenyl N Cl Et Et NMe₂ 2-chlorophenyl N Cl H CO₂Me NMe₂2-chlorophenyl N Cl Me Et NMe₂ 2-chlorophenyl N Cl Et Me NMe₂2-chlorophenyl N Cl CH₂CH═CH₂ H NMe₂ 2-chlorophenyl N Cl H CH₂CH═CH₂NMe₂ 2-chlorophenyl N Cl CH₂CCH H NMe₂ 2-chlorophenyl N Cl H CH₂CCH NMe₂2-chlorophenyl N Cl iso-Pr H NMe₂ 2-chlorophenyl N Cl H iso-Pr NMe₂2-chlorophenyl N Cl H 2- NMe₂ 2-chlorophenyl N Cl pyridinyl H 3- NMe₂2-chlorophenyl N Cl pyridinyl H 4- NMe₂ 2-chlorophenyl N Cl pyridinyl—(CH₂)₃— NMe₂ 2-chlorophenyl N Cl —(CH₂)₄— NMe₂ 2-chlorophenyl N Cl H HNMe₂ 2-chlorophenyl N Br Me H NMe₂ 2-chlorophenyl N Br H Me NMe₂2-chlorophenyl N Br Me Me NMe₂ 2-chlorophenyl N Br Et H NMe₂2-chlorophenyl N Br H Et NMe₂ 2-chlorophenyl N Br Et Et NMe₂2-chlorophenyl N Br H CO₂Me NMe₂ 2-chlorophenyl N Br Me Et NMe₂2-chlorophenyl N Br Et Me NMe₂ 2-chlorophenyl N Br CH₂CH═CH₂ H NMe₂2-chlorophenyl N Br H CH₂CH═CH₂ NMe₂ 2-chlorophenyl N Br CH₂CCH H NMe₂2-chlorophenyl N Br H CH₂CCH NMe₂ 2-chlorophenyl N Br iso-Pr H NMe₂2-chlorophenyl N Br H iso-Pr NMe₂ 2-chlorophenyl N Br H 2- NMe₂2-chlorophenyl N Br pyridinyl H 3- NMe₂ 2-chlorophenyl N Br pyridinyl H4- NMe₂ 2-chlorophenyl N Br pyridinyl —(CH₂)₃— NMe₂ 2-chlorophenyl N Br—(CH₂)₄— NMe₂ 2-chlorophenyl N Br H H NMe₂ 2-chlorophenyl N CF₃ Me HNMe₂ 2-chlorophenyl N CF₃ H Me NMe₂ 2-chlorophenyl N CF₃ Me Me NMe₂2-chlorophenyl N CF₃ Et H NMe₂ 2-chlorophenyl N CF₃ H Et NMe₂2-chlorophenyl N CF₃ Et Et NMe₂ 2-chlorophenyl N CF₃ H CO₂Me NMe₂2-chlorophenyl N CF₃ Me Et NMe₂ 2-chlorophenyl N CF₃ Et Me NMe₂2-chlorophenyl N CF₃ CH₂CH═CH₂ H NMe₂ 2-chlorophenyl N CF₃ H CH₂CH═CH₂NMe₂ 2-chlorophenyl N CF₃ CH₂CCH H NMe₂ 2-chlorophenyl N CF₃ H CH₂CCHNMe₂ 2-chlorophenyl N CF₃ iso-Pr H NMe₂ 2-chlorophenyl N CF₃ H iso-PrNMe₂ 2-chlorophenyl N CF₃ H 2- NMe₂ 2-chlorophenyl N CF₃ pyridinyl H 3-NMe₂ 2-chlorophenyl N CF₃ pyridinyl H 4- NMe₂ 2-chlorophenyl N CF₃pyridinyl —(CH₂)₃— NMe₂ 2-chlorophenyl N CF₃ —(CH₂)₄— NMe₂2-chlorophenyl N CF₃ H H H 2,6- N Cl dichlorophenyl Me H H 2,6- N Cldichlorophenyl H Me H 2,6- N Cl dichlorophenyl Me Me H 2,6- N Cldichlorophenyl Et H H 2,6- N Cl dichlorophenyl H Et H 2,6- N Cldichlorophenyl Et Et H 2,6- N Cl dichlorophenyl H CO₂Me H 2,6- N Cldichlorophenyl Me Et H 2,6- N Cl dichlorophenyl Et Me H 2,6- N Cldichlorophenyl CH₂CH═CH₂ H H 2,6- N Cl dichlorophenyl H CH₂CH═CH₂ H 2,6-N Cl dichlorophenyl CH₂CCH H H 2,6- N Cl dichlorophenyl H CH₂CCH H 2,6-N Cl dichlorophenyl iso-Pr H H 2,6- N Cl dichlorophenyl H iso-Pr H 2,6-N Cl dichlorophenyl H 2- H 2,6- N Cl pyridinyl dichlorophenyl H 3- H2,6- N Cl pyridinyl dichlorophenyl H 4- H 2,6- N Cl pyridinyldichlorophenyl —(CH₂)₃— H 2,6- N Cl dichlorophenyl —(CH₂)₄— H 2,6- N Cldichlorophenyl H H H 2,6- N Br dichlorophenyl Me H H 2,6- N Brdichlorophenyl H Me H 2,6- N Br dichlorophenyl Me Me H 2,6- N Brdichlorophenyl Et H H 2,6- N Br dichlorophenyl H Et H 2,6- N Brdichlorophenyl Et Et H 2,6- N Br dichlorophenyl H CO₂Me H 2,6- N Brdichlorophenyl Me Et H 2,6- N Br dichlorophenyl Et Me H 2,6- N Brdichlorophenyl CH₂CH═CH₂ H H 2,6- N Br dichlorophenyl H CH₂CH═CH₂ H 2,6-N Br dichlorophenyl CH₂CCH H H 2,6- N Br dichlorophenyl H CH₂CCH H 2,6-N Br dichlorophenyl iso-Pr H H 2,6- N Br dichlorophenyl H iso-Pr H 2,6-N Br dichlorophenyl H 2- H 2,6- N Br pyridinyl dichlorophenyl H 3- H2,6- N Br pyridinyl dichlorophenyl H 4- H 2,6- N Br pyridinyldichlorophenyl —(CH₂)₃— H 2,6- N Br dichlorophenyl —(CH₂)₄— H 2,6- N Brdichlorophenyl H H H 2,6- N CF₃ dichlorophenyl Me H H 2,6- N CF₃dichlorophenyl H Me H 2,6- N CF₃ dichlorophenyl Me Me H 2,6- N CF₃dichlorophenyl Et H H 2,6- N CF₃ dichlorophenyl H Et H 2,6- N CF₃dichlorophenyl Et Et H 2,6- N CF₃ dichlorophenyl H CO₂Me H 2,6- N CF₃dichlorophenyl Me Et H 2,6- N CF₃ dichlorophenyl Et Me H 2,6- N CF₃dichlorophenyl CH₂CH═CH₂ H H 2,6- N CF₃ dichlorophenyl H CH₂CH═CH₂ H2,6- N CF₃ dichlorophenyl CH₂CCH H H 2,6- N CF₃ dichlorophenyl H CH₂CCHH 2,6- N CF₃ dichlorophenyl iso-Pr H H 2,6- N CF₃ dichlorophenyl Hiso-Pr H 2,6- N CF₃ dichlorophenyl H 2- H 2,6- N CF₃ pyridinyldichlorophenyl H 3- H 2,6- N CF₃ pyridinyl dichlorophenyl H 4- H 2,6- NCF₃ pyridinyl dichlorophenyl —(CH₂)₃— H 2,6- N CF₃ dichlorophenyl—(CH₂)₄— H 2,6- N CF₃ dichlorophenyl H H OMe 2,6- N Cl dichlorophenyl MeH OMe 2,6- N Cl dichlorophenyl H Me OMe 2,6- N Cl dichlorophenyl Me MeOMe 2,6- N Cl dichlorophenyl Et H OMe 2,6- N Cl dichlorophenyl H Et OMe2,6- N Cl dichlorophenyl Et Et OMe 2,6- N Cl dichlorophenyl H CO₂Me OMe2,6- N Cl dichlorophenyl Me Et OMe 2,6- N Cl dichlorophenyl Et Me OMe2,6- N Cl dichlorophenyl CH₂CH═CH₂ H OMe 2,6- N Cl dichlorophenyl HCH₂CH═CH₂ OMe 2,6- N Cl dichlorophenyl CH₂CCH H OMe 2,6- N Cldichlorophenyl H CH₂CCH OMe 2,6- N Cl dichlorophenyl iso-Pr H OMe 2,6- NCl dichlorophenyl H iso-Pr OMe 2,6- N Cl dichlorophenyl H 2- OMe 2,6- NCl pyridinyl dichlorophenyl H 3- OMe 2,6- N Cl pyridinyl dichlorophenylH 4- OMe 2,6- N Cl pyridinyl dichlorophenyl —(CH₂)₃— OMe 2,6- N Cldichlorophenyl —(CH₂)₄— OMe 2,6- N Cl dichlorophenyl H H OMe 2,6- N Brdichlorophenyl Me H OMe 2,6- N Br dichlorophenyl H Me OMe 2,6- N Brdichlorophenyl Me Me OMe 2,6- N Br dichlorophenyl Et H OMe 2,6- N Brdichlorophenyl H Et OMe 2,6- N Br dichlorophenyl Et Et OMe 2,6- N Brdichlorophenyl H CO₂Me OMe 2,6- N Br dichlorophenyl Me Et OMe 2,6- N Brdichlorophenyl Et Me OMe 2,6- N Br dichlorophenyl CH₂CH═CH₂ H OMe 2,6- NBr dichlorophenyl H CH₂CH═CH₂ OMe 2,6- N Br dichlorophenyl CH₂CCH H OMe2,6- N Br dichlorophenyl H CH₂CCH OMe 2,6- N Br dichlorophenyl iso-Pr HOMe 2,6- N Br dichlorophenyl H iso-Pr OMe 2,6- N Br dichlorophenyl H 2-OMe 2,6- N Br pyridinyl dichlorophenyl H 3- OMe 2,6- N Br pyridinyldichlorophenyl H 4- OMe 2,6- N Br pyridinyl dichlorophenyl —(CH₂)₃— OMe2,6- N Br dichlorophenyl —(CH₂)₄— OMe 2,6- N Br dichlorophenyl H H OMe2,6- N CF₃ dichlorophenyl Me H OMe 2,6- N CF₃ dichlorophenyl H Me OMe2,6- N CF₃ dichlorophenyl Me Me OMe 2,6- N CF₃ dichlorophenyl Et H OMe2,6- N CF₃ dichlorophenyl H Et OMe 2,6- N CF₃ dichlorophenyl Et Et OMe2,6- N CF₃ dichlorophenyl H CO₂Me OMe 2,6- N CF₃ dichlorophenyl Me EtOMe 2,6- N CF₃ dichlorophenyl Et Me OMe 2,6- N CF₃ dichlorophenylCH₂CH═CH₂ H OMe 2,6- N CF₃ dichlorophenyl H CH₂CH═CH₂ OMe 2,6- N CF₃dichlorophenyl CH₂CCH H OMe 2,6- N CF₃ dichlorophenyl H CH₂CCH OMe 2,6-N CF₃ dichlorophenyl iso-Pr H OMe 2,6- N CF₃ dichlorophenyl H iso-Pr OMe2,6- N CF₃ dichlorophenyl H 2- OMe 2,6- N CF₃ pyridinyl dichlorophenyl H3- OMe 2,6- N CF₃ pyridinyl dichlorophenyl H 4- OMe 2,6- N CF₃ pyridinyldichlorophenyl —(CH₂)₃— OMe 2,6- N CF₃ dichlorophenyl —(CH₂)₄— OMe 2,6-N CF₃ dichlorophenyl H H NHMe 2,6- N Cl dichlorophenyl Me H NHMe 2,6- NCl dichlorophenyl H Me NHMe 2,6- N Cl dichlorophenyl Me Me NHMe 2,6- NCl dichlorophenyl Et H NHMe 2,6- N Cl dichlorophenyl H Et NHMe 2,6- N Cldichlorophenyl Et Et NHMe 2,6- N Cl dichlorophenyl H CO₂Me NHMe 2,6- NCl dichlorophenyl Me Et NHMe 2,6- N Cl dichlorophenyl Et Me NHMe 2,6- NCl dichlorophenyl CH₂CH═CH₂ H NHMe 2,6- N Cl dichlorophenyl H CH₂CH═CH₂NHMe 2,6- N Cl dichlorophenyl CH₂CCH H NHMe 2,6- N Cl dichlorophenyl HCH₂CCH NHMe 2,6- N Cl dichlorophenyl iso-Pr H NHMe 2,6- N Cldichlorophenyl H iso-Pr NHMe 2,6- N Cl dichlorophenyl H 2- NHMe 2,6- NCl pyridinyl dichlorophenyl H 3- NHMe 2,6- N Cl pyridinyl dichlorophenylH 4- NHMe 2,6- N Cl pyridinyl dichlorophenyl —(CH₂)₃— NHMe 2,6- N Cldichlorophenyl —(CH₂)₄— NHMe 2,6- N Cl dichlorophenyl H H NHMe 2,6- N Brdichlorophenyl Me H NHMe 2,6- N Br dichlorophenyl H Me NHMe 2,6- N Brdichlorophenyl Me Me NHMe 2,6- N Br dichlorophenyl Et H NHMe 2,6- N Brdichlorophenyl H Et NHMe 2,6- N Br dichlorophenyl Et Et NHMe 2,6- N Brdichlorophenyl H CO₂Me NHMe 2,6- N Br dichlorophenyl Me Et NHMe 2,6- NBr dichlorophenyl Et Me NHMe 2,6- N Br dichlorophenyl CH₂CH═CH₂ H NHMe2,6- N Br dichlorophenyl H CH₂CH═CH₂ NHMe 2,6- N Br dichlorophenylCH₂CCH H NHMe 2,6- N Br dichlorophenyl H CH₂CCH NHMe 2,6- N Brdichlorophenyl iso-Pr H NHMe 2,6- N Br dichlorophenyl H iso-Pr NHMe 2,6-N Br dichlorophenyl H 2- NHMe 2,6- N Br pyridinyl dichlorophenyl H 3-NHMe 2,6- N Br pyridinyl dichlorophenyl H 4- NHMe 2,6- N Br pyridinyldichlorophenyl —(CH₂)₃— NHMe 2,6- N Br dichlorophenyl —(CH₂)₄— NHMe 2,6-N Br dichlorophenyl H H NHMe 2,6- N CF₃ dichlorophenyl Me H NHMe 2,6- NCF₃ dichlorophenyl H Me NHMe 2,6- N CF₃ dichlorophenyl Me Me NHMe 2,6- NCF₃ dichlorophenyl Et H NHMe 2,6- N CF₃ dichlorophenyl H Et NHMe 2,6- NCF₃ dichlorophenyl Et Et NHMe 2,6- N CF₃ dichlorophenyl H CO₂Me NHMe2,6- N CF₃ dichlorophenyl Me Et NHMe 2,6- N CF₃ dichlorophenyl Et MeNHMe 2,6- N CF₃ dichlorophenyl CH₂CH═CH₂ H NHMe 2,6- N CF₃dichlorophenyl H CH₂CH═CH₂ NHMe 2,6- N CF₃ dichlorophenyl CH₂CCH H NHMe2,6- N CF₃ dichlorophenyl H CH₂CCH NHMe 2,6- N CF₃ dichlorophenyl iso-PrH NHMe 2,6- N CF₃ dichlorophenyl H iso-Pr NHMe 2,6- N CF₃ dichlorophenylH 2- NHMe 2,6- N CF₃ pyridinyl dichlorophenyl H 3- NHMe 2,6- N CF₃pyridinyl dichlorophenyl H 4- NHMe 2,6- N CF₃ pyridinyl dichlorophenyl—(CH₂)₃— NHMe 2,6- N CF₃ dichlorophenyl —(CH₂)₄— NHMe 2,6- N CF₃dichlorophenyl H H NMe₂ 2,6- N Cl dichlorophenyl Me H NMe₂ 2,6- N Cldichlorophenyl H Me NMe₂ 2,6- N Cl dichlorophenyl Me Me NMe₂ 2,6- N Cldichlorophenyl Et H NMe₂ 2,6- N Cl dichlorophenyl H Et NMe₂ 2,6- N Cldichlorophenyl Et Et NMe₂ 2,6- N Cl dichlorophenyl H CO₂Me NMe₂ 2,6- NCl dichlorophenyl Me Et NMe₂ 2,6- N Cl dichlorophenyl Et Me NMe₂ 2,6- NCl dichlorophenyl CH₂CH═CH₂ H NMe₂ 2,6- N Cl dichlorophenyl H CH₂CH═CH₂NMe₂ 2,6- N Cl dichlorophenyl CH₂CCH H NMe₂ 2,6- N Cl dichlorophenyl HCH₂CCH NMe₂ 2,6- N Cl dichlorophenyl iso-Pr H NMe₂ 2,6- N Cldichlorophenyl H iso-Pr NMe₂ 2,6- N Cl dichlorophenyl H 2- NMe₂ 2,6- NCl pyridinyl dichlorophenyl H 3- NMe₂ 2,6- N Cl pyridinyl dichlorophenylH 4- NMe₂ 2,6- N Cl pyridinyl dichlorophenyl —(CH₂)₃— NMe₂ 2,6- N Cldichlorophenyl —(CH₂)₄— NMe₂ 2,6- N Cl dichlorophenyl H H NMe₂ 2,6- N Brdichlorophenyl Me H NMe₂ 2,6- N Br dichlorophenyl H Me NMe₂ 2,6- N Brdichlorophenyl Me Me NMe₂ 2,6- N Br dichlorophenyl Et H NMe₂ 2,6- N Brdichlorophenyl H Et NMe₂ 2,6- N Br dichlorophenyl Et Et NMe₂ 2,6- N Brdichlorophenyl H CO₂Me NMe₂ 2,6- N Br dichlorophenyl Me Et NMe₂ 2,6- NBr dichlorophenyl Et Me NMe₂ 2,6- N Br dichlorophenyl CH₂CH═CH₂ H NMe₂2,6- N Br dichlorophenyl H CH₂CH═CH₂ NMe₂ 2,6- N Br dichlorophenylCH₂CCH H NMe₂ 2,6- N Br dichlorophenyl H CH₂CCH NMe₂ 2,6- N Brdichlorophenyl iso-Pr H NMe₂ 2,6- N Br dichlorophenyl H iso-Pr NMe₂ 2,6-N Br dichlorophenyl H 2- NMe₂ 2,6- N Br pyridinyl dichlorophenyl H 3-NMe₂ 2,6- N Br pyridinyl dichlorophenyl H 4- NMe₂ 2,6- N Br pyridinyldichlorophenyl —(CH₂)₃— NMe₂ 2,6- N Br dichlorophenyl —(CH₂)₄— NMe₂ 2,6-N Br dichlorophenyl H H NMe₂ 2,6- N CF₃ dichlorophenyl Me H NMe₂ 2,6- NCF₃ dichlorophenyl H Me NMe₂ 2,6- N CF₃ dichlorophenyl Me Me NMe₂ 2,6- NCF₃ dichlorophenyl Et H NMe₂ 2,6- N CF₃ dichlorophenyl H Et NMe₂ 2,6- NCF₃ dichlorophenyl Et Et NMe₂ 2,6- N CF₃ dichlorophenyl H CO₂Me NMe₂2,6- N CF₃ dichlorophenyl Me Et NMe₂ 2,6- N CF₃ dichlorophenyl Et MeNMe₂ 2,6- N CF₃ dichlorophenyl CH₂CH═CH₂ H NMe₂ 2,6- N CF₃dichlorophenyl H CH₂CH═CH₂ NMe₂ 2,6- N CF₃ dichlorophenyl CH₂CCH H NMe₂2,6- N CF₃ dichlorophenyl H CH₂CCH NMe₂ 2,6- N CF₃ dichlorophenyl iso-PrH NMe₂ 2,6- N CF₃ dichlorophenyl H iso-Pr NMe₂ 2,6- N CF₃ dichlorophenylH 2- NMe₂ 2,6- N CF₃ pyridinyl dichlorophenyl H 3- NMe₂ 2,6- N CF₃pyridinyl dichlorophenyl H 4- NMe₂ 2,6- N CF₃ pyridinyl dichlorophenyl—(CH₂)₃— NMe₂ 2,6- N CF₃ dichlorophenyl —(CH₂)₄— NMe₂ 2,6- N CF₃dichlorophenyl H H H Me N Cl Me H H Me N Cl H Me H Me N Cl Me Me H Me NCl Et H H Me N Cl H Et H Me N Cl Et Et H Me N Cl H CO₂Me H Me N Cl Me EtH Me N Cl Et Me H Me N Cl CH₂CH═CH₂ H H Me N Cl H CH₂CH═CH₂ H Me N ClCH₂CCH H H Me N Cl H CH₂CCH H Me N Cl iso-Pr H H Me N Cl H iso-Pr H Me NCl H 2- H Me N Cl pyridinyl H 3- H Me N Cl pyridinyl H 4- H Me N Clpyridinyl —(CH₂)₃— H Me N Cl —(CH₂)₄— H Me N Cl H H H Me N Br Me H H MeN Br H Me H Me N Br Me Me H Me N Br Et H H Me N Br H Et H Me N Br Et EtH Me N Br H CO₂Me H Me N Br Me Et H Me N Br Et Me H Me N Br CH₂CH═CH₂ HH Me N Br H CH₂CH═CH₂ H Me N Br CH₂CCH H H Me N Br H CH₂CCH H Me N Briso-Pr H H Me N Br H iso-Pr H Me N Br H 2- H Me N Br pyridinyl H 3- H MeN Br pyridinyl H 4- H Me N Br pyridinyl —(CH₂)₃— H Me N Br —(CH₂)₄— H MeN Br H H H Me N CF₃ Me H H Me N CF₃ H Me H Me N CF₃ Me Me H Me N CF₃ EtH H Me N CF₃ H Et H Me N CF₃ Et Et H Me N CF₃ H CO₂Me H Me N CF₃ Me Et HMe N CF₃ Et Me H Me N CF₃ CH₂CH═CH₂ H H Me N CF₃ H CH₂CH═CH₂ H Me N CF₃CH₂CCH H H Me N CF₃ H CH₂CCH H Me N CF₃ iso-Pr H H Me N CF₃ H iso-Pr HMe N CF₃ H 2- H Me N CF₃ pyridinyl H 3- H Me N CF₃ pyridinyl H 4- H Me NCF₃ pyridinyl —(CH₂)₃— H Me N CF₃ —(CH₂)₄— H Me N CF₃ H H OMe Me N Cl MeH OMe Me N Cl H Me OMe Me N Cl Me Me OMe Me N Cl Et H OMe Me N Cl H EtOMe Me N Cl Et Et OMe Me N Cl H CO₂Me OMe Me N Cl Me Et OMe Me N Cl EtMe OMe Me N Cl CH₂CH═CH₂ H OMe Me N Cl H CH₂CH═CH₂ OMe Me N Cl CH₂CCH HOMe Me N Cl H CH₂CCH OMe Me N Cl iso-Pr H OMe Me N Cl H iso-Pr OMe Me NCl H 2- OMe Me N Cl pyridinyl H 3- OMe Me N Cl pyridinyl H 4- OMe Me NCl pyridinyl —(CH₂)₃— OMe Me N Cl —(CH₂)₄— OMe Me N Cl H H OMe Me N BrMe H OMe Me N Br H Me OMe Me N Br Me Me OMe Me N Br Et H OMe Me N Br HEt OMe Me N Br Et Et OMe Me N Br H CO₂Me OMe Me N Br Me Et OMe Me N BrEt Me OMe Me N Br CH₂CH═CH₂ H OMe Me N Br H CH₂CH═CH₂ OMe Me N Br CH₂CCHH OMe Me N Br H CH₂CCH OMe Me N Br iso-Pr H OMe Me N Br H iso-Pr OMe MeN Br H 2- OMe Me N Br pyridinyl H 3- OMe Me N Br pyridinyl H 4- OMe Me NBr pyridinyl —(CH₂)₃— OMe Me N Br —(CH₂)₄— OMe Me N Br H H OMe Me N CF₃Me H OMe Me N CF₃ H Me OMe Me N CF₃ Me Me OMe Me N CF₃ Et H OMe Me N CF₃H Et OMe Me N CF₃ Et Et OMe Me N CF₃ H CO₂Me OMe Me N CF₃ Me Et OMe Me NCF₃ Et Me OMe Me N CF₃ CH₂CH═CH₂ H OMe Me N CF₃ H CH₂CH═CH₂ OMe Me N CF₃CH₂CCH H OMe Me N CF₃ H CH₂CCH OMe Me N CF₃ iso-Pr H OMe Me N CF₃ Hiso-Pr OMe Me N CF₃ H 2- OMe Me N CF₃ pyridinyl H 3- OMe Me N CF₃pyridinyl H 4- OMe Me N CF₃ pyridinyl —(CH₂)₃— OMe Me N CF₃ —(CH₂)₄— OMeMe N CF₃ H H NHMe Me N Cl Me H NHMe Me N Cl H Me NHMe Me N Cl Me Me NHMeMe N Cl Et H NHMe Me N Cl H Et NHMe Me N Cl Et Et NHMe Me N Cl H CO₂MeNHMe Me N Cl Me Et NHMe Me N Cl Et Me NHMe Me N Cl CH₂CH═CH₂ H NHMe Me NCl H CH₂CH═CH₂ NHMe Me N Cl CH₂CCH H NHMe Me N Cl H CH₂CCH NHMe Me N Cliso-Pr H NHMe Me N Cl H iso-Pr NHMe Me N Cl H 2- NHMe Me N Cl pyridinylH 3- NHMe Me N Cl pyridinyl H 4- NHMe Me N Cl pyridinyl —(CH₂)₃— NHMe MeN Cl —(CH₂)₄— NHMe Me N Cl H H NHMe Me N Br Me H NHMe Me N Br H Me NHMeMe N Br Me Me NHMe Me N Br Et H NHMe Me N Br H Et NHMe Me N Br Et EtNHMe Me N Br H CO₂Me NHMe Me N Br Me Et NHMe Me N Br Et Me NHMe Me N BrCH₂CH═CH₂ H NHMe Me N Br H CH₂CH═CH₂ NHMe Me N Br CH₂CCH H NHMe Me N BrH CH₂CCH NHMe Me N Br iso-Pr H NHMe Me N Br H iso-Pr NHMe Me N Br H 2-NHMe Me N Br pyridinyl H 3- NHMe Me N Br pyridinyl H 4- NHMe Me N Brpyridinyl —(CH₂)₃— NHMe Me N Br —(CH₂)₄— NHMe Me N Br H H NHMe Me N CF₃Me H NHMe Me N CF₃ H Me NHMe Me N CF₃ Me Me NHMe Me N CF₃ Et H NHMe Me NCF₃ H Et NHMe Me N CF₃ Et Et NHMe Me N CF₃ H CO₂Me NHMe Me N CF₃ Me EtNHMe Me N CF₃ Et Me NHMe Me N CF₃ CH₂CH═CH₂ H NHMe Me N CF₃ H CH₂CH═CH₂NHMe Me N CF₃ CH₂CCH H NHMe Me N CF₃ H CH₂CCH NHMe Me N CF₃ iso-Pr HNHMe Me N CF₃ H iso-Pr NHMe Me N CF₃ H 2- NHMe Me N CF₃ pyridinyl H 3-NHMe Me N CF₃ pyridinyl H 4- NHMe Me N CF₃ pyridinyl —(CH₂)₃— NHMe Me NCF₃ —(CH₂)₄— NHMe Me N CF₃ H H NMe₂ Me N Cl Me H NMe₂ Me N Cl H Me NMe₂Me N Cl Me Me NMe₂ Me N Cl Et H NMe₂ Me N Cl H Et NMe₂ Me N Cl Et EtNMe₂ Me N Cl H CO₂Me NMe₂ Me N Cl Me Et NMe₂ Me N Cl Et Me NMe₂ Me N ClCH₂CH═CH₂ H NMe₂ Me N Cl H CH₂CH═CH₂ NMe₂ Me N Cl CH₂CCH H NMe₂ Me N ClH CH₂CCH NMe₂ Me N Cl iso-Pr H NMe₂ Me N Cl H iso-Pr NMe₂ Me N Cl H 2-NMe₂ Me N Cl pyridinyl H 3- NMe₂ Me N Cl pyridinyl H 4- NMe₂ Me N Clpyridinyl —(CH₂)₃— NMe₂ Me N Cl —(CH₂)₄— NMe₂ Me N Cl H H NMe₂ Me N BrMe H NMe₂ Me N Br H Me NMe₂ Me N Br Me Me NMe₂ Me N Br Et H NMe₂ Me N BrH Et NMe₂ Me N Br Et Et NMe₂ Me N Br H CO₂Me NMe₂ Me N Br Me Et NMe₂ MeN Br Et Me NMe₂ Me N Br CH₂CH═CH₂ H NMe₂ Me N Br H CH₂CH═CH₂ NMe₂ Me NBr CH₂CCH H NMe₂ Me N Br H CH₂CCH NMe₂ Me N Br iso-Pr H NMe₂ Me N Br Hiso-Pr NMe₂ Me N Br H 2- NMe₂ Me N Br pyridinyl H 3- NMe₂ Me N Brpyridinyl H 4- NMe₂ Me N Br pyridinyl —(CH₂)₃— NMe₂ Me N Br —(CH₂)₄—NMe₂ Me N Br H H NMe₂ Me N CF₃ Me H NMe₂ Me N CF₃ H Me NMe₂ Me N CF₃ MeMe NMe₂ Me N CF₃ Et H NMe₂ Me N CF₃ H Et NMe₂ Me N CF₃ Et Et NMe₂ Me NCF₃ H CO₂Me NMe₂ Me N CF₃ Me Et NMe₂ Me N CF₃ Et Me NMe₂ Me N CF₃CH₂CH═CH₂ H NMe₂ Me N CF₃ H CH₂CH═CH₂ NMe₂ Me N CF₃ CH₂CCH H NMe₂ Me NCF₃ H CH₂CCH NMe₂ Me N CF₃ iso-Pr H NMe₂ Me N CF₃ H iso-Pr NMe₂ Me N CF₃H 2- NMe₂ Me N CF₃ pyridinyl H 3- NMe₂ Me N CF₃ pyridinyl H 4- NMe₂ Me NCF₃ pyridinyl —(CH₂)₃— NMe₂ Me N CF₃ —(CH₂)₄— NMe₂ Me N CF₃ H H H Et NCl Me H H Et N Cl H Me H Et N Cl Me Me H Et N Cl Et H H Et N Cl H Et HEt N Cl Et Et H Et N Cl H CO₂Me H Et N Cl Me Et H Et N Cl Et Me H Et NCl CH₂CH═CH₂ H H Et N Cl H CH₂CH═CH₂ H Et N Cl CH₂CCH H H Et N Cl HCH₂CCH H Et N Cl iso-Pr H H Et N Cl H iso-Pr H Et N Cl H 2- H Et N Clpyridinyl H 3- H Et N Cl pyridinyl H 4- H Et N Cl pyridinyl —(CH₂)₃— HEt N Cl —(CH₂)₄— H Et N Cl H H H Et N Br Me H H Et N Br H Me H Et N BrMe Me H Et N Br Et H H Et N Br H Et H Et N Br Et Et H Et N Br H CO₂Me HEt N Br Me Et H Et N Br Et Me H Et N Br CH₂CH═CH₂ H H Et N Br HCH₂CH═CH₂ H Et N Br CH₂CCH H H Et N Br H CH₂CCH H Et N Br iso-Pr H H EtN Br H iso-Pr H Et N Br H 2- H Et N Br pyridinyl H 3- H Et N Brpyridinyl H 4- H Et N Br pyridinyl —(CH₂)₃— H Et N Br —(CH₂)₄— H Et N BrH H H Et N CF₃ Me H H Et N CF₃ H Me H Et N CF₃ Me Me H Et N CF₃ Et H HEt N CF₃ H Et H Et N CF₃ Et Et H Et N CF₃ H CO₂Me H Et N CF₃ Me Et H EtN CF₃ Et Me H Et N CF₃ CH₂CH═CH₂ H H Et N CF₃ H CH₂CH═CH₂ H Et N CF₃CH₂CCH H H Et N CF₃ H CH₂CCH H Et N CF₃ iso-Pr H H Et N CF₃ H iso-Pr HEt N CF₃ H 2- H Et N CF₃ pyridinyl H 3- H Et N CF₃ pyridinyl H 4- H Et NCF₃ pyridinyl —(CH₂)₃— H Et N CF₃ —(CH₂)₄— H Et N CF₃ H H OMe Et N Cl MeH OMe Et N Cl H Me OMe Et N Cl Me Me OMe Et N Cl Et H OMe Et N Cl H EtOMe Et N Cl Et Et OMe Et N Cl H CO₂Me OMe Et N Cl Me Et OMe Et N Cl EtMe OMe Et N Cl CH₂CH═CH₂ H OMe Et N Cl H CH₂CH═CH₂ OMe Et N Cl CH₂CCH HOMe Et N Cl H CH₂CCH OMe Et N Cl iso-Pr H OMe Et N Cl H iso-Pr OMe Et NCl H 2- OMe Et N Cl pyridinyl H 3- OMe Et N Cl pyridinyl H 4- OMe Et NCl pyridinyl —(CH₂)₃— OMe Et N Cl —(CH₂)₄— OMe Et N Cl H H OMe Et N BrMe H OMe Et N Br H Me OMe Et N Br Me Me OMe Et N Br Et H OMe Et N Br HEt OMe Et N Br Et Et OMe Et N Br H CO₂Me OMe Et N Br Me Et OMe Et N BrEt Me OMe Et N Br CH₂CH═CH₂ H OMe Et N Br H CH₂CH═CH₂ OMe Et N Br CH₂CCHH OMe Et N Br H CH₂CCH OMe Et N Br iso-Pr H OMe Et N Br H iso-Pr OMe EtN Br H 2- OMe Et N Br pyridinyl H 3- OMe Et N Br pyridinyl H 4- OMe Et NBr pyridinyl —(CH₂)₃— OMe Et N Br —(CH₂)₄— OMe Et N Br H H OMe Et N CF₃Me H OMe Et N CF₃ H Me OMe Et N CF₃ Me Me OMe Et N CF₃ Et H OMe Et N CF₃H Et OMe Et N CF₃ Et Et OMe Et N CF₃ H CO₂Me OMe Et N CF₃ Me Et OMe Et NCF₃ Et Me OMe Et N CF₃ CH₂CH═CH₂ H OMe Et N CF₃ H CH₂CH═CH₂ OMe Et N CF₃CH₂CCH H OMe Et N CF₃ H CH₂CCH OMe Et N CF₃ iso-Pr H OMe Et N CF₃ Hiso-Pr OMe Et N CF₃ H 2- OMe Et N CF₃ pyridinyl H 3- OMe Et N CF₃pyridinyl H 4- OMe Et N CF₃ pyridinyl —(CH₂)₃— OMe Et N CF₃ —(CH₂)₄— OMeEt N CF₃ H H NHMe Et N Cl Me H NHMe Et N Cl H Me NHMe Et N Cl Me Me NHMeEt N Cl Et H NHMe Et N Cl H Et NHMe Et N Cl Et Et NHMe Et N Cl H CO₂MeNHMe Et N Cl Me Et NHMe Et N Cl Et Me NHMe Et N Cl CH₂CH═CH₂ H NHMe Et NCl H CH₂CH═CH₂ NHMe Et N Cl CH₂CCH H NHMe Et N Cl H CH₂CCH NHMe Et N Cliso-Pr H NHMe Et N Cl H iso-Pr NHMe Et N Cl H 2- NHMe Et N Cl pyridinylH 3- NHMe Et N Cl pyridinyl H 4- NHMe Et N Cl pyridinyl —(CH₂)₃— NHMe EtN Cl —(CH₂)₄— NHMe Et N Cl H H NHMe Et N Br Me H NHMe Et N Br H Me NHMeEt N Br Me Me NHMe Et N Br Et H NHMe Et N Br H Et NHMe Et N Br Et EtNHMe Et N Br H CO₂Me NHMe Et N Br Me Et NHMe Et N Br Et Me NHMe Et N BrCH₂CH═CH₂ H NHMe Et N Br H CH₂CH═CH₂ NHMe Et N Br CH₂CCH H NHMe Et N BrH CH₂CCH NHMe Et N Br iso-Pr H NHMe Et N Br H iso-Pr NHMe Et N Br H 2-NHMe Et N Br pyridinyl H 3- NHMe Et N Br pyridinyl H 4- NHMe Et N Brpyridinyl —(CH₂)₃— NHMe Et N Br —(CH₂)₄— NHMe Et N Br H H NHMe Et N CF₃Me H NHMe Et N CF₃ H Me NHMe Et N CF₃ Me Me NHMe Et N CF₃ Et H NHMe Et NCF₃ H Et NHMe Et N CF₃ Et Et NHMe Et N CF₃ H CO₂Me NHMe Et N CF₃ Me EtNHMe Et N CF₃ Et Me NHMe Et N CF₃ CH₂CH═CH₂ H NHMe Et N CF₃ H CH₂CH═CH₂NHMe Et N CF₃ CH₂CCH H NHMe Et N CF₃ H CH₂CCH NHMe Et N CF₃ iso-Pr HNHMe Et N CF₃ H iso-Pr NHMe Et N CF₃ H 2- NHMe Et N CF₃ pyridinyl H 3-NHMe Et N CF₃ pyridinyl H 4- NHMe Et N CF₃ pyridinyl —(CH₂)₃— NHMe Et NCF₃ —(CH₂)₄— NHMe Et N CF₃ H H NMe₂ Et N Cl Me H NMe₂ Et N Cl H Me NMe₂Et N Cl Me Me NMe₂ Et N Cl Et H NMe₂ Et N Cl H Et NMe₂ Et N Cl Et EtNMe₂ Et N Cl H CO₂Me NMe₂ Et N Cl Me Et NMe₂ Et N Cl Et Me NMe₂ Et N ClCH₂CH═CH₂ H NMe₂ Et N Cl H CH₂CH═CH₂ NMe₂ Et N Cl CH₂CCH H NMe₂ Et N ClH CH₂CCH NMe₂ Et N Cl iso-Pr H NMe₂ Et N Cl H iso-Pr NMe₂ Et N Cl H 2-NMe₂ Et N Cl pyridinyl H 3- NMe₂ Et N Cl pyridinyl H 4- NMe₂ Et N Clpyridinyl —(CH₂)₃— NMe₂ Et N Cl —(CH₂)₄— NMe₂ Et N Cl H H NMe₂ Et N BrMe H NMe₂ Et N Br H Me NMe₂ Et N Br Me Me NMe₂ Et N Br Et H NMe₂ Et N BrH Et NMe₂ Et N Br Et Et NMe₂ Et N Br H CO₂Me NMe₂ Et N Br Me Et NMe₂ EtN Br Et Me NMe₂ Et N Br CH₂CH═CH₂ H NMe₂ Et N Br H CH₂CH═CH₂ NMe₂ Et NBr CH₂CCH H NMe₂ Et N Br H CH₂CCH NMe₂ Et N Br iso-Pr H NMe₂ Et N Br Hiso-Pr NMe₂ Et N Br H 2- NMe₂ Et N Br pyridinyl H 3- NMe₂ Et N Brpyridinyl H 4- NMe₂ Et N Br pyridinyl —(CH₂)₃— NMe₂ Et N Br —(CH₂)₄—NMe₂ Et N Br H H NMe₂ Et N CF₃ Me H NMe₂ Et N CF₃ H Me NMe₂ Et N CF₃ MeMe NMe₂ Et N CF₃ Et H NMe₂ Et N CF₃ H Et NMe₂ Et N CF₃ Et Et NMe₂ Et NCF₃ H CO₂Me NMe₂ Et N CF₃ Me Et NMe₂ Et N CF₃ Et Me NMe₂ Et N CF₃CH₂CH═CH₂ H NMe₂ Et N CF₃ H CH₂CH═CH₂ NMe₂ Et N CF₃ CH₂CCH H NMe₂ Et NCF₃ H CH₂CCH NMe₂ Et N CF₃ iso-Pr H NMe₂ Et N CF₃ H iso-Pr NMe₂ Et N CF₃H 2- NMe₂ Et N CF₃ pyridinyl H 3- NMe₂ Et N CF₃ pyridinyl H 4- NMe₂ Et NCF₃ pyridinyl —(CH₂)₃— NMe₂ Et N CF₃ —(CH₂)₄— NMe₂ Et N CF₃ H H H iso-PrN Cl Me H H iso-Pr N Cl H Me H iso-Pr N Cl Me Me H iso-Pr N Cl Et H Hiso-Pr N Cl H Et H iso-Pr N Cl Et Et H iso-Pr N Cl H CO₂Me H iso-Pr N ClMe Et H iso-Pr N Cl Et Me H iso-Pr N Cl CH₂CH═CH₂ H H iso-Pr N Cl HCH₂CH═CH₂ H iso-Pr N Cl CH₂CCH H H iso-Pr N Cl H CH₂CCH H iso-Pr N Cliso-Pr H H iso-Pr N Cl H iso-Pr H iso-Pr N Cl H 2- H iso-Pr N Clpyridinyl H 3- H iso-Pr N Cl pyridinyl H 4- H iso-Pr N Cl pyridinyl—(CH₂)₃— H iso-Pr N Cl —(CH₂)₄— H iso-Pr N Cl H H H iso-Pr N Br Me H Hiso-Pr N Br H Me H iso-Pr N Br Me Me H iso-Pr N Br Et H H iso-Pr N Br HEt H iso-Pr N Br Et Et H iso-Pr N Br H CO₂Me H iso-Pr N Br Me Et Hiso-Pr N Br Et Me H iso-Pr N Br CH₂CH═CH₂ H H iso-Pr N Br H CH₂CH═CH₂ Hiso-Pr N Br CH₂CCH H H iso-Pr N Br H CH₂CCH H iso-Pr N Br iso-Pr H Hiso-Pr N Br H iso-Pr H iso-Pr N Br H 2- H iso-Pr N Br pyridinyl H 3- Hiso-Pr N Br pyridinyl H 4- H iso-Pr N Br pyridinyl —(CH₂)₃— H iso-Pr NBr —(CH₂)₄— H iso-Pr N Br H H H iso-Pr N CF₃ Me H H iso-Pr N CF₃ H Me Hiso-Pr N CF₃ Me Me H iso-Pr N CF₃ Et H H iso-Pr N CF₃ H Et H iso-Pr NCF₃ Et Et H iso-Pr N CF₃ H CO₂Me H iso-Pr N CF₃ Me Et H iso-Pr N CF₃ EtMe H iso-Pr N CF₃ CH₂CH═CH₂ H H iso-Pr N CF₃ H CH₂CH═CH₂ H iso-Pr N CF₃CH₂CCH H H iso-Pr N CF₃ H CH₂CCH H iso-Pr N CF₃ iso-Pr H H iso-Pr N CF₃H iso-Pr H iso-Pr N CF₃ H 2- H iso-Pr N CF₃ pyridinyl H 3- H iso-Pr NCF₃ pyridinyl H 4- H iso-Pr N CF₃ pyridinyl —(CH₂)₃— H iso-Pr N CF₃—(CH₂)₄— H iso-Pr N CF₃ H H OMe iso-Pr N Cl Me H OMe iso-Pr N Cl H MeOMe iso-Pr N Cl Me Me OMe iso-Pr N Cl Et H OMe iso-Pr N Cl H Et OMeiso-Pr N Cl Et Et OMe iso-Pr N Cl H CO₂Me OMe iso-Pr N Cl Me Et OMeiso-Pr N Cl Et Me OMe iso-Pr N Cl CH₂CH═CH₂ H OMe iso-Pr N Cl HCH₂CH═CH₂ OMe iso-Pr N Cl CH₂CCH H OMe iso-Pr N Cl H CH₂CCH OMe iso-Pr NCl iso-Pr H OMe iso-Pr N Cl H iso-Pr OMe iso-Pr N Cl H 2- OMe iso-Pr NCl pyridinyl H 3- OMe iso-Pr N Cl pyridinyl H 4- OMe iso-Pr N Clpyridinyl —(CH₂)₃— OMe iso-Pr N Cl —(CH₂)₄— OMe iso-Pr N Cl H H OMeiso-Pr N Br Me H OMe iso-Pr N Br H Me OMe iso-Pr N Br Me Me OMe iso-Pr NBr Et H OMe iso-Pr N Br H Et OMe iso-Pr N Br Et Et OMe iso-Pr N Br HCO₂Me OMe iso-Pr N Br Me Et OMe iso-Pr N Br Et Me OMe iso-Pr N BrCH₂CH═CH₂ H OMe iso-Pr N Br H CH₂CH═CH₂ OMe iso-Pr N Br CH₂CCH H OMeiso-Pr N Br H CH₂CCH OMe iso-Pr N Br iso-Pr H OMe iso-Pr N Br H iso-PrOMe iso-Pr N Br H 2- OMe iso-Pr N Br pyridinyl H 3- OMe iso-Pr N Brpyridinyl H 4- OMe iso-Pr N Br pyridinyl —(CH₂)₃— OMe iso-Pr N Br—(CH₂)₄— OMe iso-Pr N Br H H OMe iso-Pr N CF₃ Me H OMe iso-Pr N CF₃ H MeOMe iso-Pr N CF₃ Me Me OMe iso-Pr N CF₃ Et H OMe iso-Pr N CF₃ H Et OMeiso-Pr N CF₃ Et Et OMe iso-Pr N CF₃ H CO₂Me OMe iso-Pr N CF₃ Me Et OMeiso-Pr N CF₃ Et Me OMe iso-Pr N CF₃ CH₂CH═CH₂ H OMe iso-Pr N CF₃ HCH₂CH═CH₂ OMe iso-Pr N CF₃ CH₂CCH H OMe iso-Pr N CF₃ H CH₂CCH OMe iso-PrN CF₃ iso-Pr H OMe iso-Pr N CF₃ H iso-Pr OMe iso-Pr N CF₃ H 2- OMeiso-Pr N CF₃ pyridinyl H 3- OMe iso-Pr N CF₃ pyridinyl H 4- OMe iso-Pr NCF₃ pyridinyl —(CH₂)₃— OMe iso-Pr N CF₃ —(CH₂)₄— OMe iso-Pr N CF₃ H HNHMe iso-Pr N Cl Me H NHMe iso-Pr N Cl H Me NHMe iso-Pr N Cl Me Me NHMeiso-Pr N Cl Et H NHMe iso-Pr N Cl H Et NHMe iso-Pr N Cl Et Et NHMeiso-Pr N Cl H CO₂Me NHMe iso-Pr N Cl Me Et NHMe iso-Pr N Cl Et Me NHMeiso-Pr N Cl CH₂CH═CH₂ H NHMe iso-Pr N Cl H CH₂CH═CH₂ NHMe iso-Pr N ClCH₂CCH H NHMe iso-Pr N Cl H CH₂CCH NHMe iso-Pr N Cl iso-Pr H NHMe iso-PrN Cl H iso-Pr NHMe iso-Pr N Cl H 2- NHMe iso-Pr N Cl pyridinyl H 3- NHMeiso-Pr N Cl pyridinyl H 4- NHMe iso-Pr N Cl pyridinyl —(CH₂)₃— NHMeiso-Pr N Cl —(CH₂)₄— NHMe iso-Pr N Cl H H NHMe iso-Pr N Br Me H NHMeiso-Pr N Br H Me NHMe iso-Pr N Br Me Me NHMe iso-Pr N Br Et H NHMeiso-Pr N Br H Et NHMe iso-Pr N Br Et Et NHMe iso-Pr N Br H CO₂Me NHMeiso-Pr N Br Me Et NHMe iso-Pr N Br Et Me NHMe iso-Pr N Br CH₂CH═CH₂ HNHMe iso-Pr N Br H CH₂CH═CH₂ NHMe iso-Pr N Br CH₂CCH H NHMe iso-Pr N BrH CH₂CCH NHMe iso-Pr N Br iso-Pr H NHMe iso-Pr N Br H iso-Pr NHMe iso-PrN Br H 2- NHMe iso-Pr N Br pyridinyl H 3- NHMe iso-Pr N Br pyridinyl H4- NHMe iso-Pr N Br pyridinyl —(CH₂)₃— NHMe iso-Pr N Br —(CH₂)₄— NHMeiso-Pr N Br H H NHMe iso-Pr N CF₃ Me H NHMe iso-Pr N CF₃ H Me NHMeiso-Pr N CF₃ Me Me NHMe iso-Pr N CF₃ Et H NHMe iso-Pr N CF₃ H Et NHMeiso-Pr N CF₃ Et Et NHMe iso-Pr N CF₃ H CO₂Me NHMe iso-Pr N CF₃ Me EtNHMe iso-Pr N CF₃ Et Me NHMe iso-Pr N CF₃ CH₂CH═CH₂ H NHMe iso-Pr N CF₃H CH₂CH═CH₂ NHMe iso-Pr N CF₃ CH₂CCH H NHMe iso-Pr N CF₃ H CH₂CCH NHMeiso-Pr N CF₃ iso-Pr H NHMe iso-Pr N CF₃ H iso-Pr NHMe iso-Pr N CF₃ H 2-NHMe iso-Pr N CF₃ pyridinyl H 3- NHMe iso-Pr N CF₃ pyridinyl H 4- NHMeiso-Pr N CF₃ pyridinyl —(CH₂)₃— NHMe iso-Pr N CF₃ —(CH₂)₄— NHMe iso-Pr NCF₃ H H NMe₂ iso-Pr N Cl Me H NMe₂ iso-Pr N Cl H Me NMe₂ iso-Pr N Cl MeMe NMe₂ iso-Pr N Cl Et H NMe₂ iso-Pr N Cl H Et NMe₂ iso-Pr N Cl Et EtNMe₂ iso-Pr N Cl H CO₂Me NMe₂ iso-Pr N Cl Me Et NMe₂ iso-Pr N Cl Et MeNMe₂ iso-Pr N Cl CH₂CH═CH₂ H NMe₂ iso-Pr N Cl H CH₂CH═CH₂ NMe₂ iso-Pr NCl CH₂CCH H NMe₂ iso-Pr N Cl H CH₂CCH NMe₂ iso-Pr N Cl iso-Pr H NMe₂iso-Pr N Cl H iso-Pr NMe₂ iso-Pr N Cl H 2- NMe₂ iso-Pr N Cl pyridinyl H3- NMe₂ iso-Pr N Cl pyridinyl H 4- NMe₂ iso-Pr N Cl pyridinyl —(CH₂)₃—NMe₂ iso-Pr N Cl —(CH₂)₄— NMe₂ iso-Pr N Cl H H NMe₂ iso-Pr N Br Me HNMe₂ iso-Pr N Br H Me NMe₂ iso-Pr N Br Me Me NMe₂ iso-Pr N Br Et H NMe₂iso-Pr N Br H Et NMe₂ iso-Pr N Br Et Et NMe₂ iso-Pr N Br H CO₂Me NMe₂iso-Pr N Br Me Et NMe₂ iso-Pr N Br Et Me NMe₂ iso-Pr N Br CH₂CH═CH₂ HNMe₂ iso-Pr N Br H CH₂CH═CH₂ NMe₂ iso-Pr N Br CH₂CCH H NMe₂ iso-Pr N BrH CH₂CCH NMe₂ iso-Pr N Br iso-Pr H NMe₂ iso-Pr N Br H iso-Pr NMe₂ iso-PrN Br H 2- NMe₂ iso-Pr N Br pyridinyl H 3- NMe₂ iso-Pr N Br pyridinyl H4- NMe₂ iso-Pr N Br pyridinyl —(CH₂)₃— NMe₂ iso-Pr N Br —(CH₂)₄— NMe₂iso-Pr N Br H H NMe₂ iso-Pr N CF₃ Me H NMe₂ iso-Pr N CF₃ H Me NMe₂iso-Pr N CF₃ Me Me NMe₂ iso-Pr N CF₃ Et H NMe₂ iso-Pr N CF₃ H Et NMe₂iso-Pr N CF₃ Et Et NMe₂ iso-Pr N CF₃ H CO₂Me NMe₂ iso-Pr N CF₃ Me EtNMe₂ iso-Pr N CF₃ Et Me NMe₂ iso-Pr N CF₃ CH₂CH═CH₂ H NMe₂ iso-Pr N CF₃H CH₂CH═CH₂ NMe₂ iso-Pr N CF₃ CH₂CCH H NMe₂ iso-Pr N CF₃ H CH₂CCH NMe₂iso-Pr N CF₃ iso-Pr H NMe₂ iso-Pr N CF₃ H iso-Pr NMe₂ iso-Pr N CF₃ H 2-NMe₂ iso-Pr N CF₃ pyridinyl H 3- NMe₂ iso-Pr N CF₃ pyridinyl H 4- NMe₂iso-Pr N CF₃ pyridinyl —(CH₂)₃— NMe₂ iso-Pr N CF₃ —(CH₂)₄— NMe₂ iso-Pr NCF₃

Compound 65:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 66:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 67:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 68:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 69:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 70:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 71:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 72:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 73:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 74:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 75:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 76:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 77:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 78:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 79:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 80:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 81:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 82:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 83:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 84:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 85:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 86:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 87:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 88:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 89:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 90:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 91:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 92:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 93:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 94:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 95:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 96:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 97:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 98:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 99:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 100:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 101:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 102:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 103:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 104:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 105:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 106:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 107:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 108:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 109:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 110:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 111:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 112:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 113:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 114:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 115:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 116:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 117:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 118:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 119:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 120:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 121:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 122:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 123:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 124:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 125:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 126:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 127:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

Compound 128:

Compounds of formula 2A wherein R², R³, M and R^(20ay) corresponds to arow in Table B, and E substituted with (R⁴)_(n) is:

TABLE B No. R² R³ M R^(20ay) H H H CHF₂ Me H H CHF₂ H Me H CHF₂ Me Me HCHF₂ Et H H CHF₂ H Et H CHF₂ Et Et H CHF₂ H CO₂ Me H CHF₂ H H OMe CHF₂Me H OMe CHF₂ H Me OMe CHF₂ Me Me OMe CHF₂ Et H OMe CHF₂ H Et OMe CHF₂Et Et OMe CHF₂ H CO₂ Me OMe CHF₂ H H NMe₂ CHF₂ Me H NMe₂ CHF₂ H Me NMe₂CHF₂ Me Me NMe₂ CHF₂ Et H NMe₂ CHF₂ H Et NMe₂ CHF₂ Et Et NMe₂ CHF₂ H CO₂Me NMe₂ CHF₂ H H NHMe CHF₂ Me H NHMe CHF₂ H Me NHMe CHF₂ Me Me NHMe CHF₂Et H NHMe CHF₂ H Et NHMe CHF₂ Et Et NHMe CHF₂ H CO₂ Me NHMe CHF₂ H H HCBrF₂ Me H H CBrF₂ H Me H CBrF₂ Me Me H CBrF₂ Et H H CBrF₂ H Et H CBrF₂Et Et H CBrF₂ H CO₂ Me H CBrF₂ H H OMe CBrF₂ Me H OMe CBrF₂ H Me OMeCBrF₂ Me Me OMe CBrF₂ Et H OMe CBrF₂ H Et OMe CBrF₂ Et Et OMe CBrF₂ HCO₂ Me OMe CBrF₂ H H NMe₂ CBrF₂ Me H NMe₂ CBrF₂ H Me NMe₂ CBrF₂ Me MeNMe₂ CBrF₂ Et H NMe₂ CBrF₂ H Et NMe₂ CBrF₂ Et Et NMe₂ CBrF₂ H CO₂ MeNMe₂ CBrF₂ H H NHMe CBrF₂ Me H NHMe CBrF₂ H Me NHMe CBrF₂ Me Me NHMeCBrF₂ Et H NHMe CBrF₂ H Et NHMe CBrF₂ Et Et NHMe CBrF₂ H CO₂ Me NHMeCBrF₂ H H H CH₂CF₂ Me H H CH₂CF₂ H Me H CH₂CF₂ Me Me H CH₂CF₂ Et H HCH₂CF₂ H Et H CH₂CF₂ Et Et H CH₂CF₂ H CO₂ Me H CH₂CF₂ H H OMe CH₂CF₂ MeH OMe CH₂CF₂ H Me OMe CH₂CF₂ Me Me OMe CH₂CF₂ Et H OMe CH₂CF₂ H Et OMeCH₂CF₂ Et Et OMe CH₂CF₂ H CO₂ Me OMe CH₂CF₂ H H NMe₂ CH₂CF₂ Me H NMe₂CH₂CF₂ H Me NMe₂ CH₂CF₂ Me Me NMe₂ CH₂CF₂ Et H NMe₂ CH₂CF₂ H Et NMe₂CH₂CF₂ Et Et NMe₂ CH₂CF₂ H CO₂ Me NMe₂ CH₂CF₂ H H NHMe CH₂CF₂ Me H NHMeCH₂CF₂ H Me NHMe CH₂CF₂ Me Me NHMe CH₂CF₂ Et H NHMe CH₂CF₂ H Et NHMeCH₂CF₂ Et Et NHMe CH₂CF₂ H CO₂ Me NHMe CH₂CF₂

Compound 129:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 130:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 131:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 132:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 133:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 134:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 135:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 136:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 137:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 138:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 139:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 140:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 141:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 142:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 143:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 144:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 145:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 146:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 147:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 148:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 149:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 150:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 151:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 152:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 153:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 154:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 155:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 156:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 157:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 158:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 159:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 160:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 161:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 162:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 163:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 164:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 165:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 166:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 167:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 168:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 169:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 170:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 171:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 172:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 173:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 174:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 175:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 176:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 177:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 178:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 179:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 180:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 181:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 182:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 183:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 184:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 185:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 186:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 187:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 188:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 189:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 190:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 191:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

Compound 192:

Compounds of formula 3A wherein R², R³, M and R^(20ax) corresponds to arow in Table C, and E substituted with (R⁴)_(n) is:

TABLE C No. R² R³ M R^(20ax) H H H CHF₂ Me H H CHF₂ H Me H CHF₂ Me Me HCHF₂ Et H H CHF₂ H Et H CHF₂ Et Et H CHF₂ H CO₂ Me H CHF₂ H H OMe CHF₂Me H OMe CHF₂ H Me OMe CHF₂ Me Me OMe CHF₂ Et H OMe CHF₂ H Et OMe CHF₂Et Et OMe CHF₂ H CO₂ Me OMe CHF₂ H H NMe₂ CHF₂ Me H NMe₂ CHF₂ H Me NMe₂CHF₂ Me Me NMe₂ CHF₂ Et H NMe₂ CHF₂ H Et NMe₂ CHF₂ Et Et NMe₂ CHF₂ H CO₂Me NMe₂ CHF₂ H H NHMe CHF₂ Me H NHMe CHF₂ ' H Me NHMe CHF₂ Me Me NHMeCHF₂ Et H NHMe CHF₂ H Et NHMe CHF₂ Et Et NHMe CHF₂ H CO₂ Me NHMe CHF₂ HH H CBrF₂ Me H H CBrF₂ H Me H CBrF₂ Me Me H CBrF₂ Et H H CBrF₂ H Et HCBrF₂ Et Et H CBrF₂ H CO₂ Me H CBrF₂ H H OMe CBrF₂ Me H OMe CBrF₂ H MeOMe CBrF₂ Me Me OMe CBrF₂ Et H OMe CBrF₂ H Et OMe CBrF₂ Et Et OMe CBrF₂H CO₂ Me OMe CBrF₂ H H NMe₂ CBrF₂ Me H NMe₂ CBrF₂ H Me NMe₂ CBrF₂ Me MeNMe₂ CBrF₂ Et H NMe₂ CBrF₂ H Et NMe₂ CBrF₂ Et Et NMe₂ CBrF₂ H CO₂ MeNMe₂ CBrF₂ H H NHMe CBrF₂ Me H NHMe CBrF₂ H Me NHMe CBrF₂ Me Me NHMeCBrF₂ Et H NHMe CBrF₂ H Et NHMe CBrF₂ Et Et NHMe CBrF₂ H CO₂ Me NHMeCBrF₂ H H H CH₂CF₂ Me H H CH₂CF₂ H Me H CH₂CF₂ Me Me H CH₂CF₂ Et H HCH₂CF₂ H Et H CH₂CF₂ Et Et H CH₂CF₂ H CO₂ Me H CH₂CF₂ H H OMe CH₂CF₂ MeH OMe CH₂CF₂ H Me OMe CH₂CF₂ Me Me OMe CH₂CF₂ Et H OMe CH₂CF₂ H Et OMeCH₂CF₂ Et Et OMe CH₂CF₂ H CO₂ Me OMe CH₂CF₂ H H NMe₂ CH₂CF₂ Me H NMe₂CH₂CF₂ H Me NMe₂ CH₂CF₂ Me Me NMe₂ CH₂CF₂ Et H NMe₂ CH₂CF₂ H Et NMe₂CH₂CF₂ Et Et NMe₂ CH₂CF₂ H CO₂ Me NMe₂ CH₂CF₂ H H NHMe CH₂CF₂ Me H NHMeCH₂CF₂ H Me NHMe CH₂CF₂ Me Me NHMe CH₂CF₂ Et H NHMe CH₂CF₂ H Et NHMeCH₂CF₂ Et Et NHMe CH₂CF₂ H CO₂ Me NHMe CH₂CF₂

Compound 193:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 194:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 195:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 196:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 197:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 198:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 199:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 200:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 201:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 202:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 203:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 204:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 205:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 206:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 207:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 208:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 209:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 210:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 211:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 212:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 213:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 214:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 215:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 216:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 217:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 218:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 219:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 220:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 221:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 222:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 223:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 224:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 225:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 226:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 227:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 228:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 229:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 230:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 231:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 232:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 233:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 234:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 235:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 236:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 237:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 238:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 239:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 240:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 241:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 242:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 243:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 244:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 245:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 246:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 247:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 248:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 249:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 250:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 251:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 252:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 253:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 254:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 255:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 256:

Compounds of formula 4A wherein R², R³, M, R^(13a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 257:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 258:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 259:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 260:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 261:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 262:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 263:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 264:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 265:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 266:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 267:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 268:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 269:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 270:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 271:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 272:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 273:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 274:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 275:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 276:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

Compound 277:

Compounds of formula 4A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table D, and E substituted with (R⁴)_(n) is:

TABLE D R² R³ M R^(19a) R^(20ay) H H H 3-chloro-2- Cl pyridinyl Me H H3-chloro-2- Cl pyridinyl H Me H 3-chloro-2- Cl pyridinyl Me Me H3-chloro-2- Cl pyridinyl Et H H 3-chloro-2- Cl pyridinyl H Et H3-chloro-2- Cl pyridinyl Et Et H 3-chloro-2- Cl pyridinyl H CO₂ Me H3-chloro-2- Cl pyridinyl H H H 3-chloro-2- Br pyridinyl Me H H3-chloro-2- Br pyridinyl H Me H 3-chloro-2- Br pyridinyl Me Me H3-chloro-2- Br pyridinyl Et H H 3-chloro-2- Br pyridinyl H Et H3-chloro-2- Br pyridinyl Et Et H 3-chloro-2- Br pyridinyl H CO₂ Me H3-chloro-2- Br pyridinyl H H H 3-chloro-2- CF₃ pyridinyl Me H H3-chloro-2- CF₃ pyridinyl H Me H 3-chloro-2- CF₃ pyridinyl Me Me H3-chloro-2- CF₃ pyridinyl Et H H 3-chloro-2- CF₃ pyridinyl H Et H3-chloro-2- CF₃ pyridinyl Et Et H 3-chloro-2- CF₃ pyridinyl H CO₂ Me H3-chloro-2- CF₃ pyridinyl H H OMe 3-chloro-2- Cl pyridinyl Me H OMe3-chloro-2- Cl pyridinyl H Me OMe 3-chloro-2- Cl pyridinyl Me Me OMe3-chloro-2- Cl pyridinyl Et H OMe 3-chloro-2- Cl pyridinyl H Et OMe3-chloro-2- Cl pyridinyl Et Et OMe 3-chloro-2- Cl pyridinyl H CO₂ Me OMe3-chloro-2- Cl pyridinyl H H OMe 3-chloro-2- Br pyridinyl Me H OMe3-chloro-2- Br pyridinyl H Me OMe 3-chloro-2- Br pyridinyl Me Me OMe3-chloro-2- Br pyridinyl Et H OMe 3-chloro-2- Br pyridinyl H Et OMe3-chloro-2- Br pyridinyl Et Et OMe 3-chloro-2- Br pyridinyl H CO₂ Me OMe3-chloro-2- Br pyridinyl H H OMe 3-chloro-2- CF₃ pyridinyl Me H OMe3-chloro-2- CF₃ pyridinyl H Me OMe 3-chloro-2- CF₃ pyridinyl Me Me OMe3-chloro-2- CF₃ pyridinyl Et H OMe 3-chloro-2- CF₃ pyridinyl H Et OMe3-chloro-2- CF₃ pyridinyl Et Et OMe 3-chloro-2- CF₃ pyridinyl H CO₂ MeOMe 3-chloro-2- CF₃ pyridinyl

Compound 278:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 279:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 280:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 281:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 282:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 283:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 284:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 285:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 286:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 287:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 288:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 289:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 290:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 291:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 292:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 293:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 294:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 295:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 296:

Compounds of formula 5A wherein R², R³, M, R^(19a), R^(20ay) correspondsto a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 297:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 298:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 299:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 300:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 301:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 302:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 303:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 304:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 305:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 306:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 307:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 308:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 309:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 310:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 311:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 312:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 313:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 314:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 315:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 316:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 317:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 318:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 319:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 320:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 321:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 322:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 323:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 324:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 325:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 326:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 327:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 328:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 329:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 330:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 331:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 332:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 333:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 334:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 335:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 336:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 337:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 338:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 339:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 340:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

Compound 341:

Compounds of formula 5A wherein R², R³, M, R^(19a) and R^(20ay)corresponds to a row in Table E, and E substituted with (R⁴)_(n) is:

TABLE E R² R³ M R^(19a) R^(20ay) H H H 3-chloro-2- Cl pyridinyl Me H H3-chloro-2- Cl pyridinyl H Me H 3-chloro-2- Cl pyridinyl Me Me H3-chloro-2- Cl pyridinyl Et H H 3-chloro-2- Cl pyridinyl H Et H3-chloro-2- Cl pyridinyl Et Et H 3-chloro-2- Cl pyridinyl H CO₂ Me H3-chloro-2- Cl pyridinyl H H H 3-chloro-2- Br pyridinyl Me H H3-chloro-2- Br pyridinyl H Me H 3-chloro-2- Br pyridinyl Me Me H3-chloro-2- Br pyridinyl Et H H 3-chloro-2- Br pyridinyl H Et H3-chloro-2- Br pyridinyl Et Et H 3-chloro-2- Br pyridinyl H CO₂ Me H3-chloro-2- Br pyridinyl H H H 3-chloro-2- CF₃ pyridinyl Me H H3-chloro-2- CF₃ pyridinyl H Me H 3-chloro-2- CF₃ pyridinyl Me Me H3-chloro-2- CF₃ pyridinyl Et H H 3-chloro-2- CF₃ pyridinyl H Et H3-chloro-2- CF₃ pyridinyl Et Et H 3-chloro-2- CF₃ pyridinyl H CO₂ Me H3-chloro-2- CF₃ pyridinyl H H Me 3-chloro-2- Cl pyridinyl Me H Me3-chloro-2- Cl pyridinyl H Me Me 3-chloro-2- Cl pyridinyl Me Me Me3-chloro-2- Cl pyridinyl Et H Me 3-chloro-2- Cl pyridinyl H Et Me3-chloro-2- Cl pyridinyl Et Et Me 3-chloro-2- Cl pyridinyl H CO₂ Me Me3-chloro-2- Cl pyridinyl H H Me 3-chloro-2- Br pyridinyl Me H Me3-chloro-2- Br pyridinyl H Me Me 3-chloro-2- Br pyridinyl Me Me Me3-chloro-2- Br pyridinyl Et H Me 3-chloro-2- Br pyridinyl H Et Me3-chloro-2- Br pyridinyl Et Et Me 3-chloro-2- Br pyridinyl H CO₂ Me Me3-chloro-2- Br pyridinyl H H Me 3-chloro-2- CF₃ pyridinyl Me H Me3-chloro-2- CF₃ pyridinyl H Me Me 3-chloro-2- CF₃ pyridinyl Me Me Me3-chloro-2- CF₃ pyridinyl Et H Me 3-chloro-2- CF₃ pyridinyl H Et Me3-chloro-2- CF₃ pyridinyl Et Et Me 3-chloro-2- CF₃ pyridinyl H CO₂ Me Me3-chloro-2- CF₃ pyridinyl H H OMe 3-chloro-2- Cl pyridinyl Me H OMe3-chloro-2- Cl pyridinyl H Me OMe 3-chloro-2- Cl pyridinyl Me Me OMe3-chloro-2- Cl pyridinyl Et H OMe 3-chloro-2- Cl pyridinyl H Et OMe3-chloro-2- Cl pyridinyl Et Et OMe 3-chloro-2- Cl pyridinyl H CO₂ Me OMe3-chloro-2- Cl pyridinyl H H OMe 3-chloro-2- Br pyridinyl Me H OMe3-chloro-2- Br pyridinyl H Me OMe 3-chloro-2- Br pyridinyl Me Me OMe3-chloro-2- Br pyridinyl Et H OMe 3-chloro-2- Br pyridinyl H Et OMe3-chloro-2- Br pyridinyl Et Et OMe 3-chloro-2- Br pyridinyl H CO₂ Me OMe3-chloro-2- Br pyridinyl H H OMe 3-chloro-2- CF₃ pyridinyl Me H OMe3-chloro-2- CF₃ pyridinyl H Me OMe 3-chloro-2- CF₃ pyridinyl Me Me OMe3-chloro-2- CF₃ pyridinyl Et H OMe 3-chloro-2- CF₃ pyridinyl H Et OMe3-chloro-2- CF₃ pyridinyl Et Et OMe 3-chloro-2- CF₃ pyridinyl H CO₂ MeOMe 3-chloro-2- CF₃ pyridinyl H H OEt 3-chloro-2- Cl pyridinyl Me H OEt3-chloro-2- Cl pyridinyl H Me OEt 3-chloro-2- Cl pyridinyl Me Me OEt3-chloro-2- Cl pyridinyl Et H OEt 3-chloro-2- Cl pyridinyl H Et OEt3-chloro-2- Cl pyridinyl Et Et OEt 3-chlorp-2- Cl pyridinyl H CO₂ Me OEt3-chloro-2- Cl pyridinyl H H OEt 3-chloro-2- Br pyridinyl Me H OEt3-chloro-2- Br pyridinyl H Me OEt 3-chloro-2- Br pyridinyl Me Me OEt3-chloro-2- Br pyridinyl Et H OEt 3-chloro-2- Br pyridinyl H Et OEt3-chloro-2- Br pyridinyl Et Et OEt 3-chloro-2- Br pyridinyl H CO₂ Me OEt3-chloro-2- Br pyridinyl H H OEt 3-chloro-2- CF₃ pyridinyl Me H OEt3-chloro-2- CF₃ pyridinyl H Me OEt 3-chloro-2- CF₃ pyridinyl Me Me OEt3-chloro-2- CF₃ pyridinyl Et H OEt 3-chloro-2- CF₃ pyridinyl H Et OEt3-chloro-2- CF₃ pyridinyl Et Et OEt 3-chloro-2- CF₃ pyridinyl H CO₂ MeOEt 3-chloro-2- CF₃ pyridinyl H H NH₂ 3-chloro-2- Cl pyridinyl Me H NH₂3-chloro-2- Cl pyridinyl H Me NH₂ 3-chloro-2- Cl pyridinyl Me Me NH₂3-chloro-2- Cl pyridinyl Et H NH₂ 3-chloro-2- Cl pyridinyl H Et NH₂3-chloro-2- Cl pyridinyl Et Et NH₂ 3-chloro-2- Cl pyridinyl H CO₂ Me NH₂3-chloro-2- Cl pyridinyl H H NH₂ 3-chloro-2- Br pyridinyl Me H NH₂3-chloro-2- Br pyridinyl H Me NH₂ 3-chloro-2- Br pyridinyl Me Me NH₂3-chloro-2- Br pyridinyl Et H NH₂ 3-chloro-2- Br pyridinyl H Et NH₂3-chloro-2- Br pyridinyl Et Et NH₂ 3-chloro-2- Br pyridinyl H CO₂ Me NH₂3-chloro-2- Br pyridinyl H H NH₂ 3-chloro-2- CF₃ pyridinyl Me H NH₂3-chloro-2- CF₃ pyridinyl H Me NH₂ 3-chloro-2- CF₃ pyridinyl Me Me NH₂3-chloro-2- CF₃ pyridinyl Et H NH₂ 3-chloro-2- CF₃ pyridinyl H Et NH₂3-chloro-2- CF₃ pyridinyl Et Et NH₂ 3-chloro-2- CF₃ pyridinyl H CO₂ MeNH₂ 3-chloro-2- CF₃ pyridinyl H H NHMe 3-chloro-2- Cl pyridinyl Me HNHMe 3-chloro-2- Cl pyridinyl H Me NHMe 3-chloro-2- Cl pyridinyl Me MeNHMe 3-chloro-2- Cl pyridinyl Et H NHMe 3-chloro-2- Cl pyridinyl H EtNHMe 3-chloro-2- Cl pyridinyl Et Et NHMe 3-chloro-2- Cl pyridinyl H CO₂Me NHMe 3-chloro-2- Cl pyridinyl H H NHMe 3-chloro-2- Br pyridinyl Me HNHMe 3-chloro-2- Br pyridinyl H Me NHMe 3-chloro-2- Br pyridinyl Me MeNHMe 3-chloro-2- Br pyridinyl Et H NHMe 3-chloro-2- Br pyridinyl H EtNHMe 3-chloro-2- Br pyridinyl Et Et NHMe 3-chloro-2- Br pyridinyl H CO₂Me NHMe 3-chloro-2- Br pyridinyl H H NHMe 3-chloro-2- CF₃ pyridinyl Me HNHMe 3-chloro-2- CF₃ pyridinyl H Me NHMe 3-chloro-2- CF₃ pyridinyl Me MeNHMe 3-chloro-2- CF₃ pyridinyl Et H NHMe 3-chloro-2- CF₃ pyridinyl H EtNHMe 3-chloro-2- CF₃ pyridinyl Et Et NHMe 3-chloro-2- CF₃ pyridinyl HCO₂ Me NHMe 3-chloro-2- CF₃ pyridinyl H H NMe₂ 3-chloro-2- Cl pyridinylMe H NMe₂ 3-chloro-2- Cl pyridinyl H Me NMe₂ 3-chloro-2- Cl pyridinyl MeMe NMe₂ 3-chloro-2- Cl pyridinyl Et H NMe₂ 3-chloro-2- Cl pyridinyl H EtNMe₂ 3-chloro-2- Cl pyridinyl Et Et NMe₂ 3-chloro-2- Cl pyridinyl H CO₂Me NMe₂ 3-chloro-2- Cl pyridinyl H H NMe₂ 3-chloro-2- Br pyridinyl Me HNMe₂ 3-chloro-2- Br pyridinyl H Me NMe₂ 3-chloro-2- Br pyridinyl Me MeNMe₂ 3-chloro-2- Br pyridinyl Et H NMe₂ 3-chloro-2- Br pyridinyl H EtNMe₂ 3-chloro-2- Br pyridinyl Et Et NMe₂ 3-chloro-2- Br pyridinyl H CO₂Me NMe₂ 3-chloro-2- Br pyridinyl H H NMe₂ 3-chloro-2- CF₃ pyridinyl Me HNMe₂ 3-chloro-2- CF₃ pyridinyl H Me NMe₂ 3-chloro-2- CF₃ pyridinyl Me MeNMe₂ 3-chloro-2- CF₃ pyridinyl Et H NMe₂ 3-chloro-2- CF₃ pyridinyl H EtNMe₂ 3-chloro-2- CF₃ pyridinyl Et Et NMe₂ 3-chloro-2- CF₃ pyridinyl HCO₂ Me NMe₂ 3-chloro-2- CF₃ pyridinyl

Examples of the pests against which the present compound has controllingefficacy include harmful arthropods such as harmful insects and harmfulmites, and nemathelminths such as nematodes, and specific examples areas shown below.

Hemiptera:—

Planthoppers (Delphacidae) such as small brown planthopper (Laodelphaxstriatellus), brown rice planthopper (Nilaparvata lugens), andwhite-backed rice planthopper (Sogatella furcifera); leafhoppers(Deltocephalidae) such as green rice leafhopper (Nephotettixcincticeps), green rice leafhopper (Nephotettix virescens), and teagreen leafhopper (Empoasca onukii); aphids (Aphididae) such as cottonaphid (Aphis gossypii), green peach aphid (Myzus persicae), cabbageaphid (Brevicoryne brassicae), spiraea aphid (Aphis spiraecola), potatoaphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani), oatbird-cherry aphid (Rhopalosiphum padi), tropical citrus aphid (Toxopteracitricidus), and mealy plum aphid (Hyalopterus pruni); stink bugs(Pentatomidae) such as green stink bug (Nezara antennata), bean bug(Riptortus clavetus), rice bug (Leptocorisa chinensis), white spottedspined bug (Eysarcoris parvus), and stink bug (Halyomorpha mista);whiteflies (Aleyrodidae) such as greenhouse whitefly (Trialeurodesvaporariorum), sweetpotato whitefly (Bemisia tabaci), silver leafwhitefly (Bemisia argentifolii), citrus whitefly (Dialeurodes citri),and citrus spiny white fly (Aleurocanthus spiniferus); scales (Coccidae)such as California red scale (Aonidiella aurantii), San Jose scale(Comstockaspis perniciosa), citrus north scale (Unaspis citri), red waxscale (Ceroplastes rubens), cottonycushion scale (Icerya purchasi),Japanese mealybug (Planococcus kraunhiae), Comstock mealybug(Pseudococcus longispinis), and white peach scale (Pseudaulacaspispentagona); lace bags (Tingidae); psyllids (Psyllidae); etc.

Lepidoptera:—

Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis),yellow rice borer (Tryporyza incertulas), rice leafroller(Cnaphalocrocis medinalis), cotton leafroller (Notarcha derogata),Indian meal moth (Plodia interpunctella), oriental corn borer (Ostriniafurnacalis), cabbage webworm (Hellula undalis), and bluegrass webworm(Pediasia teterrellus); owlet moths (Noctuidae) such as common cutworm(Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm(Pseudaletia separata), cabbage armyworm (Mamestra brassicae), blackcutworm (Agrotis ipsilon), beet semi-looper (Plusia nigrisigna),Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; whites andsulfer butterflies (Pieridae) such as common white (Pieris rapae);tortricid moths (Tortricidae) such as Adoxophyes spp., oriental fruitmoth (Grapholita molesta), soybean pod borer (Leguminivoraglycinivorella), azuki bean podworm (Matsumuraeses azukivora), summerfruit tortrix (Adoxophyes orana fasciata), Adoxophyes sp., oriental teatortrix (Homona magnanima), apple tortrix (Archips fuscocupreanus), andCydia pomonella; leafblotch miners (Gracillariidae) such as tealeafroller (Caloptilia theivora), and apple leafminer (Phyllonorycterringoneella); Carposimidae such as peach fruit moth (Carposinaniponensis); lyonetiid moths (Lyonetiidae) such as Lyonetia spp.;tussock moths (Lymantriidae) such as Lymantria spp., and Euproctis spp.;yponomeutid moths (Yponomeutidae) such as diamondback (Plutellaxylostella); gelechiid moths (Gelechiidae) such as pink bollworm(Pectinophora gossypiella), and potato tubeworm (Phthorimaeaoperculella); tiger moths and allies (Arctiidae) such as fall webworm(Hyphantria cunea); tineid moths (Tineidae) such as casemaking clothesmoth (Tinea translucens), and webbing clothes moth (Tineolabisselliella); etc.

Thysanoptera:—

Thrips (Thripidae) such as yellow citrus thrips (Frankliniellaoccidentalis), Thrips parmi, yellow tea thrips (Scirtothrips dorsalis),onion thrip (Thrips tabaci), flower thrips (Frankliniella intonsa), etc.

Diptera:—

Housefly (Musca domestica), common mosquito (Culex popiens pallens),horsefly (Tabanus trigonus), onion maggot (Hylemya antiqua), seedcornmaggot (Hylemya platura), Anopheles sinensis, rice leafminer (Agromyzaoryzae), rice leafminer (Hydrellia griseola), rice stem maggot (Chloropsoryzae), melon fly (Dacus cucurbitae), Ceratitis capitata, legumeleafminer (Liriomyza trifolii), tomato leafminer (Liriomyza sativae),garden pea leafminer (Chromatomyia horticola), etc.

Coleoptera:—

Twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), cucurbitleaf beetle (Aulacophora femoralis), striped flea beetle (Phyllotretastriolata), rice leaf beetle (Oulema oryzae), rice curculio(Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus),Anthonomus grandis, azuki bean weevil (Callosobruchus chinensis),Sphenophorus venatus, Japanese beetle (Popillia japonica), cupreouschafer (Anomala cuprea), corn root worm (Diabrotica spp.), Coloradobeetle (Leptinotarsa decemlineata), click beetle (Agriotes spp.),cigarette beetle (Lasioderma serricorne), varied carper beetle(Anthrenus verbasci), red flour beetle (Tribolium castaneum), powderpost beetle (Lyctus brunneus), white-spotted longicorn beetle(Anoplophora malasiaca), pine shoot beetle (Tomicus piniperda), etc.

Orthoptera:—

Asiatic locust (Locusta migratoria), African mole cricket (Gryllotalpaafricana), rice grasshopper (Oxya yezoensis), rice grasshopper (Oxyajaponica), etc.

Hymenoptera:—

Cabbage sawfly (Athalia rosae), Acromyrmex spp., fire ant (Solenopsisspp.), etc.

Nematodes:—

Rice white-tip nematode (Aphelenchoides besseyi), strawberry budnematode (Nothotylenchus acris), southern root-knot nematode(Meloidogyne incognita), northern root-knot nematode (Meloidogynehapla), Javanese root-knot nematode (Meloidogyne javanica), soybean cystnematode (Heterodera glycines), potato cyst nematode (Globoderarostochiensis), coffee root-lesion nematode (Pratylenchus coffeae),California root-lesion nematode (Pratylenchus neglectus), etc.

Dictyoptera:—

German cockroach (Blattella germanica), smokybrown cockroach(Periplaneta fuliginosa), American cockroach (Periplaneta americana),Periplaneta brunnea, oriental cockroach (Blatta orientalis), etc.

Acarina:—

Spider mites (Tetranychidae) such as two-spotted spider mite(Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai),citrus red mite (Panonychus citri), European red mite (Panonychus ulmi),and Oligonychus spp.; eriophyid mites (Eriophyidae) such as pink citrusrust mite (Aculops pelekassi), pink citrus rust mite (Phyllocoptrutacitri), tomato rust mite (Aculops lycopersici), purple tea mite(Calacarus carinatus), pink tea rust mite (Acaphylla theavagran), andEriophyes chibaensis; tarosonemid mites (Tarsonemidae) such as broadmite (Polyphagotarsonemus latus); false spider mites (Tenuipalpidae)such as Brevipalpus phoenicis; Tuckerellidae; ticks (Ixodidae) such asHaemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus,Ixodes ovatus, Ixodes persulcatus, Boophilus microplus, andRhipicephalus sanguineus; acarid mites (Acaridae) such as mold mite(Tyrophagus putrescentiae), and Tyrophagus similis; house dust mites(Pyroglyphidae) such as Dermatophagoides farinae, and Dermatophagoidesptrenyssnus; cheyletide mites (Cheyletidae) such as Cheyletus eruditus,Cheyletus malaccensis, and Cheyletus moorei; parasitoid mites(Dermanyssidae); etc.

The pesticide of the present invention may be the present compounditself but, usually, the present compound is mixed with an inert carriersuch as a solid carrier, a liquid carrier, a gaseous carrier and thelike and, if necessary, a surfactant, and other preparation additivesare added to formulate into a composition or a preparation such as anemulsion, oil, powder, granules, a wettable preparation, a flowablepreparation, microcapsules, an aerosol, a fumigant, poison bait, a resinpreparation or the like. These compositions or preparations usuallycontain 0.01 to 95% by weight of the present compound.

Examples of the solid carrier to be used include fine powders andgranules such as clays (kaolin clay, diatomaceous earth, bentonite,fubasami clay, acid clay, etc.), synthetic hydrous silicon oxide, talc,ceramic, other inorganic minerals (sericite, quartz, sulfur, activecarbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers(ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammoniumchloride, etc.) and the like.

Examples of the liquid carrier include water, alcohols (methanol,ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethyleneglycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone,methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons(toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane,methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane,kerosene, gas oil, etc.), esters (ethyl acetate, butyl acetate,isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyladipate, propylene glycol monomethyl ether acetate, etc.), nitriles(acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether,1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethylether, diethylene glycol monomethyl ether, propylene glycol monomethylether, dipropylene glycol monomethyl ether,3-methoxyl-3-methyl-1-butanol, etc.), acid amides(N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenatedhydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride,etc.), sulfoxides (dimethyl sulfoxide, etc.), carbonic propylene andvegetable oils (soybean oil, cottonseed oil, etc.).

Examples of the gaseous carrier include fluorocarbon, butane gas, LPG(liquefied petroleum gas), dimethyl ether, and carbonic acid gas.

Examples of the surfactant include nonionic surfactants such aspolyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether,polyethylene glycol fatty acid ester, and the like, and anionicsurfactants such as alkyl sulfonate salts, alkylbenzene sulfonate saltsand alkyl sulfate salts.

Examples of other preparation additives include binders, dispersingagents, coloring agents and stabilizers, specifically, casein, gelatin,sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.),lignin derivatives, bentonite, synthetic water-soluble polymers(polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP(acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol),and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and3-tert-butyl-4-methoxyphenol).

The method of controlling a pest of the present invention is usuallyperformed by applying the pesticide of the present invention directly toa pest or to a place where a pest inhabits (plant, soil, in house,animal, etc.).

When the pesticide of the present invention is used for controlling apest in the agricultural field, an amount to be applied is usually 1 to10,000 g per 10,000 m² in terms of the amount of the present compound.When the pesticide of the present invention is formulated into anemulsion, a wettable preparation, a flowable preparation or the like,usually, the agent is applied by diluting with water so that the activeingredient concentration becomes 0.01 to 10,000 ppm, and granules,powder or the like are usually applied as they are.

These preparations, or preparations diluted with water may be directlyapplied to a pest or to a plant such as a crop to be protected against apest, or may be applied to soil of a cultivated land in order to controla pest inhabiting in the soil.

Alternatively, treatment may be performed for example, by winding asheet-like or string-like-processed resin preparation on a crop,surrounding a crop with the resin preparation, or laying the resinpreparation on soil about roots of a crop.

When the pesticide of the present invention is used for controlling apest which inhabits in a house (e.g. fly, mosquito, cockroach, etc.),the amount to be applied is usually 0.01 to 1000 mg per 1 m² of treatingarea in terms of the amount of the present compound in case of surfacetreatment, and is usually 0.01 to 500 mg per 1 m³ of treating space interms of the amount of the present of compound in case of spatialtreatment. When the pesticide of the present invention is formulatedinto an emulsion, a wettable preparation, a flowable preparation or thelike, usually, the agent is applied by diluting with water so that theactive ingredient concentration becomes 0.1 to 1000 ppm, and oil, anaerosol, a fumigant, poison bait or the like is applied as it is.

The pesticide of the present invention may contain other harmfularthropod controlling agents, acaricides, nematicides, fungicides,herbicides, plant growth regulators, synergists, fertilizers, soilconditioners, animal feeds, and the like.

As the active ingredients of the aforementioned other harmful arthropodcontrolling agents, acaricides and/or nematicides, for example, thefollowing compounds can be mentioned.

(1) Organic Phosphorus Compounds

Acephate, aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos,chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos: CYAP,diazinon, DCIP (dichlorodiisopropyl ether), dichlofenthion: ECP,dichlorvos: DDVP, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate,formothion, hydrogen phosphide, isofenphos, isoxathion, malathion,mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP,oxydeprofos:ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl,pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos,prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos,tetrachlorvinphos, terbufos, thiometon, trichlorphon:DEP, vamidothion,and the like.

(2) Carbamate Compounds

Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran,carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb,fenoxycarb, furathiocarb, isoprocarb:MIPC, metolcarb, methomyl,methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb,xylylcarb, and the like.

(3) Synthetic Pyrethroid Compounds

Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin,cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin,esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate,flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin,permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin,silafluofen, tefluthrin, tralomethrin, transfluthrin,2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate,2,3,5,6-tetrafluoro-4-methylbenzyl(EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate,2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate,and the like.

(4) Nereistoxin Compounds

Cartap, bensultap, thiocyclam, monosultap, bisultap, and the like.

(5) Neonicotinoid Compounds

Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid,dinotefuran, clothianidin, and the like.

(6) Benzoylurea Compounds

Chlorfluazuron, bistrifluoron, diafenthiuron, diflubenzuron, fluazuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron, triflumuron, and the like.

(7) Phenylpyrazole Compounds

Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole,and the like.

(8) Bt Toxin Insecticides

Viable endospores derived from Bacillus thuringiensis and crystallinetoxins produced by it, as well as a mixture of thereof.

(9) Hydrazine Compounds

Chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and thelike.

(10) Organic Chlorine Compounds

Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, and the like.

(11) Natural Insecticides

Machine oil, nicotine-sulfate, and the like.

(12) Other Insecticides

Avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine,1,3-Dichloropropene, emamectin-benzoate, fenazaquin, flupyrazofos,hydroprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine,pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate,flubendiamide, SI-0009, cyflumetofen, arsenic acid, benclothiaz, calciumcyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim,flonicamid, flurimfen, formetanate, metam-ammonium, metam-sodium, Methylbromide, nidinotefuran, Potassium oleate, protrifenbute, spiromesifen,sulfur, metaflumizone, spirotetramat, and the like.

Acaricides

Acequinocyl, amitraz, benzoximate, bromopropylate, chinomethionat,chlorobenzilate, CPCBS (chlorfenson), clofentezine, Kelthane(dicofol),etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim,fluproxyfen, hexythiazox, propargite:BPPS, polynactins, pyridaben,Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, amidoflumet,Bifenazate, Cyflumetofen, and the like.

Nematicides (Nematicidal Active Ingredients)

DCIP, fosthiazate, levamisol, methylsothiocyanate, morantel tartarate,and the like.

The present invention will be explained in more detail below by way ofPreparation Examples, Formulation Examples, Test Examples, but thepresent invention is not limited to these Examples.

First, Preparation Examples of the present compound will be explained.

PREPARATION EXAMPLES Example 1 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-21′-pyrazole-3-carbonyl]-amino}-2,6-dichloro-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (1) Step 1: Preparation of pyrazole-1-sulfonic aciddimethylamide

Pyrazole (15 g) was dissolved in toluene (200 mL) and dimethylsulfamoylchloride (23.7 mL) was slowly added. After addition of triethylamine (40mL), the solution was stirred for 18 h at room temperature. Theprecipitate was filtered off, the filtrate concentrated in vacuum andthe residue purified by column chromatography (silica gel 60,hexane/ethyl acetate=5:1, then 2:1, R_(f)=0.30 in hexane/ethylacetate=2:1, KMnO₄-solution) to afford 17.6 g of the title compound ofthe formula

as a colorless oil.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.95 (6H, s), 6.40 (1H, dd, J=3 Hz, 2 Hz),7.75 (1H, d, J=2 Hz), 7.95 (1H, dd, J=3 Hz, 1 Hz).

Step 2: Preparation of 3-bromo-pyrazole-1-sulfonic acid dimethylamide

Pyrazole-1-sulfonc acid dimethylamide (17.6 g) was dissolved in dry THF(200 mL) and cooled to −78° C. A solution of n-butyllithium (80 mL, 1.3M) was added slowly over a period of 15 min and stirred for further 15min at −78° C. A solution of 1,2-dibromo-1,1,2,2-tetrachloroethane (35.8g) in dry THF (60 mL) was added within 10 min to this solution andstirred for further 15 min at −78° C., then the cool bath was removedand the mixture was quenched with water after stirring for 1 h. Thereaction mixture was extracted 3× with ethyl acetate, the combined org.layers were washed with brine, dried over MgSO₄ and concentrated invacuum. The residue was purified by column chromatography (silica gel60, hexane/ethyl acetate=5:1, R_(f)=0.25) to afford 21.3 g of the titlecompound of the formula

as a colorless oil.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.08 (6H, s), 6.43 (1H, m), 7.61 (1H, m).

Step 3: Preparation of 3-bromo-1H-pyrazole

To 3-bromo-pyrazole-1-sulfonic acid dimethylamide (21.3 g) was slowlyadded trifluoroacetic acid (30 mL) and stirred at room temperature for 2h. Hexane was added and the formed precipitate was filtered off andwashed with hexane. The filtrate was diluted with MTB-ether, washed withsat. NaHCO₃-solution, water and brine, dried over MgSO₄ and concentratedin vacuum to afford 10.7 g of a colorless oil containing 80% of thetitle compound of the formula

The residue was used for the next step without further purification.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.37 (1H, d, J=3 Hz), 7.55 (1H, d, J=3 Hz),12.6 (1H, br s).

Step 4: Preparation of 2-(3-bromo-pyrazol-1-yl)-3-chloro-pyridine

The crude product of 3-bromo-1H-pyrazole (10.7 g) was dissolved in DMF(80 mL), 2,3-dichloropyridine (11.8 g) and caesium carbonate (57.3 g)were added and the mixture was stirred for 8 h at 100° C. After additionof water, the mixture was extracted 2× with MTB-ether, the combined org.layers were washed 2× with water, brine, dried over MgSO₄ andconcentrated in vacuum. The residue was purified by columnchromatography (silica gel 60, hexane/ethyl acetate=5:1, R_(f)=0.20) toafford 12.9 g of the title compound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.51 (1H, d, J=3 Hz), 7.31 (1H, dd, J=8 Hz,5 Hz), 7.91 (1H, dd, J=8 Hz, 2 Hz), 8.04 (1H, d, J=3 Hz), 8.45 (1H, dd,J=5 Hz, 2 Hz).

Step 5: Preparation of5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid

2-(3-Bromo-pyrazol-1-yl)-3-chloro-pyridine (9.2 g) was dissolved in dryTHF (80 mL) and cooled to −78° C. A solution of LDA (21.3 mL, 2.0 M) wasadded over a period of 10 min and stirred for further 15 min at −78° C.The solution was poured on crushed dry ice in THF (50 mL) and stirredfor additional 1 h. Water and Et₂O were added and 2N NaOH-solution wasadded to adjust the pH to 10-12. The layers were separated and theaqueous layer was washed 2× with Et₂O and acidified with 2N HCl (pH ˜3).The resulting suspension was 3× extracted with MTB-ether, the combinedorg. layers were washed with brine, dried over MgSO₄ and concentrated toafford 7.96 g of the title compound of the formula

as an orange solid.

¹H-NMR (DMSO-d₆) δ (ppm): 7.23 (1H, s), 7.68 (1H, dd, J=8 Hz, 5 Hz),8.24 (1H, dd, J=8 Hz, 2 Hz), 8.55 (1H, dd, J=5 Hz, 2 Hz).

Step 6: Preparation of 3-aminoisonicotinic acid methyl ester

3-Aminoisonicotinic acid (400 mg) was suspended in methanol (6 mL) andtoluene (18 mL) was added. A solution of (trimethylsilyl)diazomethane(2.0 M in diethyl ether, 1.88 mL) was added slowly to the suspension.Within 5 to 10 minutes after addition, the suspension turned into asolution. After 2 hours stirring at room temperature, the reactionmixture was quenched with water and extracted 3× with ethyl acetate. Thecombined organic layer was washed with 2N hydrochloric acid, saturatedbicarbonate solution and brine, dried over MgSO₄ and concentrated invacuum. The residue was purified by column chromatography (silica gel60, hexane/ethyl acetate=1:2, R_(f)=0.40) to afford 340 mg of the titlecompound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.91 (3H, s), 5.65 (2H, br s), 7.59 (1H, d,J=5 Hz), 7.93 (1H, d, J=5 Hz), 8.19 (1H, s).

Step 7: Preparation of 3-amino-2,6-dichloroisonicotinic acid methylester

3-Aminoisonicotinic acid methyl ester (340 mg) was dissolved in DMF (3mL), N-chlorosuccinimide (600 mg) was added and the resulting solutionwas stirred for 15 hours at room temperature. The product wasprecipitated by addition of water to the reaction mixture, filtered offand washed with water. The crude product was purified by columnchromatography (silica gel 60, hexane/ethyl acetate=3:1, R_(f)=0.50) toafford 460 mg of the title compound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.94 (3H, s), 6.17 (2H, br s), 7.66 (1H,s).

Step 8: Preparation of 3-amino-2,6-dichloroisonicotinic acid

3-Amino-2,6-dichloroisonicotinic acid methyl ester (460 mg) wasdissolved in ethanol (8 mL), water (2 mL) and potassium hydroxide (234mg) was added. The solution was stirred for 20 minutes at roomtemperature and for 1.5 hours under reflux. After cooling to roomtemperature, 2N hydrochloric acid was added to adjust the pH-value to −3and the so-formed yellow precipitate was extracted 3× with ethylacetate. The combined organic layer was washed with brine, dried overMgSO₄ and concentrated in vacuum to afford 420 mg of the title compoundof the formula

as a yellow solid. The compound was used in the following reaction stepwithout further purification.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.21 (2H, br s), 7.69 (1H, s).

Step 9: Preparation of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6,8-dichloro-pyrido[3,4-d][1,3]oxazin-4-one

A mixture of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid (example 1, step 5) (745 mg) and thionyl chloride (540 μl) wasstirred under reflux for 2 hours. Excess thionyl chloride wasco-evaporated with dry toluene on a evaporator, the residue wasre-dissolved in dry acetonitrile (10 mL) and3-amino-2,6-dichloroisonicotinic acid (example 1, step 8) (745 mg) wasadded. The solution was stirred for 5 minutes at room temperature andtriethylamine (490 μL) was added and stirred for 1 hour, before a secondportion of triethylamine (490 μL) was added. After the mixture wasstirred for further 30 minutes at room temperature, methanesulfonylchloride (210 μL) was added. After stirring for 20 hours at roomtemperature, the formed precipitate was filtered off, washed carefullywith water and MTB-ether and dried in vacuum to afford 731 mg of thetitle compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.32 (1H, s), 7.51 (1H, dd, J=8 Hz, 5 Hz),7.94 (1H, s), 7.99 (1H, dd, J=8 Hz, 2 Hz), 8.55 (1H, dd, J=5 Hz, 2 Hz).

Step 10: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-2,6-dichloro-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (1)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6,8-dichloro-pyrido[3,4-d][1,3]oxazin-4-one(200 mg) was dissolved in DMF (8 mL) under slight warming up. Carbazaicacid methyl ester (380 mg) was added and the solution was stirred for 25hours at room temperature. The reaction mixture was quenched with waterand extracted with MTB-ether. The organic layer was washed 3× withwater, brine, dried over MgSO₄ and concentrated in vacuum. The residuewas purified by column chromatography (silica 60, hexane/ethylacetate=1:2, R_(f)=0.20) to afford 190 mg of compound 1 of the presentinvention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.48-3.65 (3H, m), 7.41 (1H, s), 7.60-7.63(2H, m), 8.18 (1H, d, J=8 Hz), 8.51 (1H, d, J=5 Hz), 9.47 (1H, br s),10.47 (1H, br s), 10.76 (1H, br s).

Example 2 Preparation ofN′-(2,6-dichloro-3-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (2) Step 1: Preparation of3-chloro-2-(3-trifluoromethyl-pyrazol-1-yl)-pyridine

3-Trifluoromethyl-1H-pyrazole (15.30 g), 2,3-dichloro-pyridine (16.64 g)and potassium carbonate (26.42 g) were suspended in dry DMF (100 mL) andstirred for 3 h at 130° C., overnight at rt and again for 11 h at 130°C. After complete consumption of the starting material, the reaction wascooled to room temperature and quenched with water. The mixture wasextracted 2× with ethyl acetate, the combined org. layers were washed 2×with water, brine, dried over MgSO₄ and concentrated in vacuum. Theresidue was purified by column chromatography (silica gel 60,hexane/ethyl acetate=8:1, then 5:1, R_(f)=0.35 in hexane/ethylacetate=3:1) to afford 22.88 g of the title compound of the formula

as a colorless oil.

¹H-NMR (CDCl₂, TMS) δ (ppm): 6.75 (1H, d, J=2 Hz), 7.37 (1H, dd, J=8 Hz,5 Hz), 7.95 (1H, dd, J=8 Hz, 2 Hz), 8.14 (1H, d, J=2 Hz), 8.49 (1H, dd,J=5 Hz, 2 Hz).

Step 2: Preparation of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid

3-Chloro-2-(3-trifluoromethyl-pyrazol-1-yl)-pyridine (15 g) wasdissolved in dry THF (150 mL) and cooled to −78° C. A solution of LDA(39 mL, 2.0 M) were added over a period of 15 min and stirred forfurther 15 min at −78° C. The flask was connected to a gas inlet and CO₂was bubbled through the solution in a rate that the inner temperaturewas kept below −60° C. The solution turned to pale yellow and the coolbath was removed after further 10 min stirring at −78° C. and theCO₂-stream stopped. After the solution warmed up to room temperature,200 ml water and 200 ml hexane were added, and 2N NaOH-solution wasadded to adjust the pH to 10-12. The layers were separated and theorganic layer was again 2× extracted with 0.5N NaOH-solution. Thecombined aqueous solutions were washed 2× with Et₂O and acidified with2N HCl (pH ˜3). The resulting suspension was 3× extracted withMTB-ether, the combined org. layers were washed with brine, dried overMgSO₄ and concentrated to afford 16.08 g of the title compound of theformula

as a beige solid. The compound was used for the next step withoutfurther purification.

¹H-NMR (DMSO-d₆) δ (ppm): 7.60 (1H, s), 7.74 (1H, dd, J=8 Hz, 5 Hz),8.30 (1H, dd, J=8 Hz, 2 Hz), 8.60 (1H, dd, J=5 Hz, 2 Hz).

Step 3: Preparation of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylicacid (16.08 g) was mixed with thionyl chloride (12 mL) and heated underreflux for 2 h. The excess thionyl chloride was evaporated from thecrude solution on a rotary evaporator under co-evaporation with drytoluene. The acid chloride was isolated by distillation of the residueunder reduced pressure (125° C./3 mmHg) to afford 14.2 g of the titlecompound of the formula

as a crystalline solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.52 (1H, s), 7.52 (1H, dd, J=8 Hz, 5 Hz),7.97 (1H, dd, J=8 Hz, 2 Hz), 8.53 (1H, dd, J=5 Hz, 2 Hz).

Step 4: Preparation of6,8-dichloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[3,4-d][1,3]oxazin-4-one

5-Trifluoromethyl-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid chloride (example 2, step 3) (242 mg) was added to a mixture of3-amino-2,6-dichloroisonicotinic acid (example 1, step 8) (190 mg) inacetonitrile (3 mL). The mixture was stirred for 5 minutes at roomtemperature and triethylamine (220 μL) was added and stirred for 20minutes, before a second portion of triethylamine (220 μL) was added.After the mixture was stirred for further 20 minutes at roomtemperature, methanesulfonyl chloride (70 μL) was added. After stirringfor 2 hours at room temperature, the formed precipitate was filteredoff, washed carefully with water and MTB-ether and dried in vacuum toafford 350 mg of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.54-7.57 (2H, m), 7.88 (1H, s), 8.01-8.04(1H, m), 8.56-8.58 (1H, m).

Step 5: Preparation ofN′-(2,6-dichloro-3-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (2)

6,8-Dichloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[3,4-d][1,3]oxazin-4-one(200 mg) was dissolved in DMF (5 mL), carbazaic acid methyl ester (190mg) was added and the solution was stirred for 16 hours at roomtemperature. The reaction mixture was quenched with water and extractedwith MTB-ether. The organic layer was washed 2× with water, washed withbrine, dried over MgSO₄ and concentrated in vacuum. The residue waspurified by column chromatography (silica 60, hexane/ethyl acetate=1:1,then 1:2, R_(f)=0.20 in hexane/ethyl acetate 1:2) to afford 43 mg ofcompound 2 of the present invention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.62 (3H, br s), 7.62 (1H, s), 7.67 (1H, dd,J=8 Hz, 5 Hz), 7.77 (1H, s), 8.23 (1H, d, J=8 Hz), 8.54 (1H, d, J=5 Hz),9.47 (1H, s), 10.49 (1H, s), 10.92 (1H, s).

Example 3 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-2-methyl-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (3) Step 1: preparation of(6-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester

A mixture of 5-amino-2-chloropyridine (5.0 g) and di-tert-butyldicarbonate (9.34 g) in dioxane (60 mL) was stirred for 2 hours underreflux. After cooling to room temperature, the reaction mixture wasquenched with water and extracted with ethyl acetate. The organic layerwas washed 5× with diluted hydrochloric acid, washed with saturatedsodium bicarbonate, brine, dried over MgSO₄ and concentrated in vacuum.The residue was washed with hexane to give 5.39 g of the title compoundas a white solid. The combined acidic washings were re-extracted withMTB-ether. The organic layer was washed with brine, dried over MgSO₄ andconcentrated in vacuum. The residue was combined with the residue fromthe hexane washing and purified by column chromatography (silica 60,hexane/ethyl acetate 3:1, R_(f)=0.40) to afford another 650 mg of thetitle compound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.52 (9H, s), 6.60 (1H, s), 7.25 (1H, d,J=8 Hz), 7.95-7.97 (1H, br m), 8.24 (1H, d, J=3 Hz).

Step 2: Preparation of 5-tert-butoxycarbonylamino-2-chloro-isonicotinicacid

A solution of (6-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester(4.19 g) in diethyl ether (150 mL) was cooled to −78° C. andN,N,N′,N′-tetramethylethylendiamine (6.60 g) was added. After slowaddition of n-butyl lithium solution (1.32 M in hexane, 41.6 mL) over atime period of 10 minutes, the mixture was allowed to warm up to −10°C., stirred at this temperature for 2 hours and then was re-cooled to−78° C. The mixture was poured slowly into a stirred mixture of crusheddry ice in THF and stirred for 30 minutes. The mixture was concentratedon a rotary evaporator and water was added to the residue. The aqueouslayer was washed 2× with MTB-ether and acidified with 6N hydrochloricacid to pH ˜3. The formed precipitate was filtered off, washed withwater, ethyl acetate and dried in vacuum to afford 2.46 g of the titlecompound of the formula

as a beige solid.

¹H-NMR (DMSO-D₆) δ (ppm): 1.48 (9H, s), 7.77 (1H, s), 9.13 (1H, s),10.13 (1H, s).

Step 3: Preparation of 5-amino-2-chloroisonicotinic acid

A suspension of 5-tert-butoxycarbonylamino-2-chloro-isonicotinic acid(2.46 g) in aqueous 2N potassium hydroxide solution (45 mL) was stirredat 90° C. for 5 hours. After cooling to room temperature, the solutionwas acidified by slow addition of 6N hydrochloric acid. The formedprecipitate was filtered off, washed with water, MTB-ether and hexaneand dried in vacuum to afford 700 mg of the title compound of theformula

as a beige solid.

¹H-NMR (DMSO-D₆) δ (ppm): 7.47 (1H, s), 8.02 (1H, s).

Step 4: Preparation of 5-amino-3-chloroisonicotinic acid methyl ester

5-Amino-2-chloroisonicotinic acid (1.72 g) was suspended in methanol (20mL) and toluene (60 mL) was added. A solution of(trimethylsilyl)diazomethane (2.0 M in diethyl ether, 6.5 mL) was addedslowly to the suspension. Within 5 to 10 minutes after addition, thesuspension turned into a solution. After 2 hours stirring at roomtemperature, the reaction mixture was quenched with water and extracted3× with ethyl acetate. The combined organic layer was washed withsaturated bicarbonate solution and brine, dried over MgSO₄ andconcentrated in vacuum. The residue was purified by columnchromatography (silica gel 60, chloroform/ethyl acetate=20:1, R_(f)=0.30in chloroform/ethyl acetate=3:1) to afford 1.50 g of the title compoundof the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.83 (3H, s), 6.77 (2H, s), 7.48 (1H, s), 8.05(1H, s).

Step 5: Preparation of 3-amino-2-bromo-6-chloroisonicotinic acid methylester

5-Amino-3-chloroisonicotinic acid methyl ester (600 mg) was dissolved inDMF (5 mL), N-bromosuccinimide (573 mg) was added and the solution wasstirred for 3 hours at 80° C. and hours at room temperature. Thereaction mixture was diluted with MTB-ether and 3× washed with water,washed with brine, dried over MgSO₄ and concentrated in vacuum. Theresidue was purified by column chromatography (silica 60, hexane/ethylacetate=10:1, R_(f)=0.20) to afford 787 mg of the title compound of theformula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.93 (3H, s), 6.23 (2H, br s), 7.67 (1H,s).

Step 6: Preparation of 3-amino-6-chloro-2-methylisonicotinic acid methylester

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (500 mg),potassium carbonate (829 mg), tetrakis(triphenyl phosphine)palladium(0)and trimethylboroxine (276 mg) were suspended in dioxane (15 mL). Water(1.5 mL) was added and the mixture was degassed using subsequentevaporation and flushing with nitrogen (5×). The reaction mixture wasstirred under reflux for 7 hours. After cooling to room temperature, themixture was quenched with water and extracted 2× with ethyl acetate. Thecombined organic layer was washed with brine, dried over MgSO₄ andconcentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate=3:1, R_(f)=0.25) toafford 100 mg of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.44 (3H, s), 3.92 (3H, s), 5.70 (2H, brs), 7.57 (1H, s).

Step 7: Preparation of 3-amino-6-chloro-2-methylisonicotinic acid

3-Amino-6-chloro-2-methylisonicotinic acid methyl ester (100 mg) wasdissolved in methanol (2 mL) and 2N aqueous sodium hydroxide solution (2mL) was added. The reaction mixture was stirred under reflux for 2.5hours. After cooling to room temperature, water and diethyl ether wereadded, the layers were separated and the aqueous layer was washed withdiethyl ether. The aqueous layer was acidified by addition of 2Nhydrochloric acid and the formed precipitate was 3× extracted withMTB-ether. The combined organic layer was washed with brine, dried overMgSO₄ and concentrated in vacuum to afford 89 mg of the title compoundof the formula

as a yellow solid. The crude product was used without furtherpurification in the next step.

¹H-NMR (DMSO-D₆) δ (ppm): 2.33 (3H, s), 7.40 (1H, s).

Step 8: Preparation of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,4-d][1,3]oxazin-4-one

A mixture of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid (example 1, step 5) (144 mg) and thionyl chloride (105 μl) wasstirred under reflux for 2 hours. Excess thionyl chloride wasco-evaporated with dry toluene on a evaporator, the residue re-dissolvedin dry acetonitrile (1.5 mL) and 3-amino-6-chloro-2-methylisonicotinicacid (89 mg) was added. The solution was stirred for 10 minutes at roomtemperature and triethylamine (65 μL) was added and stirred for 20minutes, before a second portion of triethylamine (130 μL) was added.After the mixture was stirred for further 20 minutes at roomtemperature, methanesulfonyl chloride (45 μL) was added. After stirringfor 48 hours at room temperature, the reaction mixture was quenched withwater and extracted 3× with ethyl acetate. The combined organic layerwas washed with brine, dried over MgSO₄ and concentrated in vacuum. Theresidue was purified by column chromatography (silica 60, hexane/ethylacetate=3:1, R_(f)=0.20) to afford 67 mg of the title compound of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.10 (3H, s), 7.28 (1H, s), 7.53 (1H, dd,J=8 Hz, 5 Hz), 7.83 (1H, s), 8.00 (1H, dd, J=8 Hz, 2 Hz), 8.56 (1H, dd,J=5 Hz, 2 Hz).

Step 9: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-2-methyl-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (3)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,4-d][1,3]oxazin-4-one(67 mg) was dissolved in DMF (4 mL) and carbazaic acid methyl ester (133mg) was added. The solution was stirred for 20 hours at roomtemperature. The reaction mixture was quenched with water and extractedwith MTB-ether. The organic layer was washed 4× with water, washed withbrine, dried over MgSO₄ and concentrated in vacuum. The residue waspurified by column chromatography (silica 60, chloroform/ethylacetate=1:1, R_(f)=0.20) to afford 61 mg of compound 3 of the presentinvention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 2.35 (3H, s), 3.48-3.63 (3H, br m), 7.36 (1H,s), 7.39 (1H, s), 7.62 (1H, dd, J=8 Hz, 5 Hz), 8.18 (1H, dd, J=8 Hz, 2Hz), 8.50 (1H, dd, J=5 Hz, 2 Hz), 9.41 (1H, s), 10.38 (1H, s), 10.47(1H, s).

Example 4 Preparation ofN′-(2-bromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (4) Step 1: Preparation of3-amino-2-bromo-6-chloroisonicotinic acid

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (260 mg) (example3, step 5) was dissolved in methanol (2 mL), 2N aqueous sodium hydroxidesolution (2 mL) was added and the reaction mixture was stirred for 2hours at reflux. After cooling to room temperature, diethyl ether andwater were added and the layers were separated. The aqueous layer waswashed with diethyl ether and acidified by addition of 2N hydrochloricacid. The formed precipitate was extracted with MTB-ether (3×), thecombined organic layer was washed with brine, dried over MgSO₄ andconcentrated in vacuum to afford 246 mg of

as a yellow solid.

¹H-NMR (DMSO-D₆) δ (ppm): 6.82 (2H, br s), 7.61 (1H, s).

Step 2: Preparation of8-bromo-2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-pyrido[3,4-d][1,3]oxazin-4-one

A mixture of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid (example 1, step 5) (1.20 g) and thionyl chloride (870 μl) wasstirred under reflux for 2 hours. Excess thionyl chloride wasco-evaporated with dry toluene on a evaporator, the residue re-dissolvedin dry acetonitrile (12 mL) and 3-amino-2-bromo-6-chloroisonicotinicacid (750 mg) was added. The solution was stirred for 10 minutes at roomtemperature and triethylamine (560 μL) was added and stirred for 20minutes, before a second portion of triethylamine (1.20 mL) was added.After the mixture was stirred for further 20 minutes at roomtemperature, methanesulfonyl chloride (340 μL) was added. After stirringfor 20 hours at room temperature, the reaction mixture was quenched byslow addition of water. The precipitate was filtered off, washed withwater/acetonitrile (1:2), acetonitrile and diethyl ether and dried invacuum to afford 598 mg of the title compound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.32 (1H, s), 7.50 (1H, dd, J=8 Hz, 5 Hz),7.94 (1H, s), 8.00 (1H, d, J=8 Hz), 8.55 (1H, d, J=5 Hz).

Step 3: Preparation ofN′-(2-bromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (4)

8-Bromo-2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-pyrido[3,4-d][1,3]oxazin-4-one(400 mg) was dissolved in DMF (12 mL) and carbazaic acid methyl ester(696 mg) was added. The solution was stirred for 22 hours at roomtemperature. The reaction mixture was quenched with water and extractedwith MTB-ether. The organic layer was washed 3× with water, brine, driedover MgSO₄ and concentrated in vacuum. The residue was purified bycolumn chromatography (silica 60, chloroform/ethyl acetate=1:1,R_(f)=0.20) to afford 330 mg of compound 4 of the present invention ofthe formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.45-3.63 (3H, br m), 7.42 (1H, s), 7.59-7.63(2H, m), 8.17 (1H, dd, J=8 Hz, 2 Hz), 8.51 (1H, dd, J=5 Hz, 2 Hz), 9.47(1H, br s), 10.44 (1H, s), 10.76 (1H, s).

Example 5 Preparation ofN′-(2,6-dibromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (5) Step 1: Preparation of pyridin-3-yl-carbamic acidtert-butyl ester

3-Aminopyridine (20.0 g) was dissolved in tert-butanol (300 mL),di-tert-butyl dicarbonate (52.0 g) was added and the solution wasstirred at 50° C. for 5 hours, then for 12 hours at room temperature andanother 7 hours at 50° C. The solvent was evaporated on a rotaryevaporator and the residue was dissolved in ethyl acetate. The organiclayer was 3× washed with water, washed with brine, dried over MgSO₄ andconcentrated in vacuum. The residue was purified 2× by columnchromatography (silica 60, hexane/ethyl acetate=1:1, then 1:2,R_(f)=0.15) to afford 6.20 g of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.53 (9H, s), 6.71 (1H, s), 7.24 (1H, dd,J=8 Hz, 5 Hz), 7.99 (1H, d, J=8 Hz), 8.28 (1H, d, J=5 Hz), 8.45 (1H, d,J=2 Hz).

Step 2: Preparation of 3-tert-butoxycarbonylamino-isonicotinic acid

Pyridin-3-yl-carbamic acid tert-butyl ester (6.20 g) was dissolved inanhydrous diethyl ether (260 mL), cooled to −78° C. andN,N,N′,N′-tetramethylethylendiamine (14.4 mL) was added. A solution ofn-butyl lithium (1.6 M in hexane, 60 mL) was added slowly over a timeperiod of 10 minutes. After the addition of the reagent was completed,the reaction mixture was allowed to warm to −10° C. and stirred at thistemperature for 2 hours. The reaction mixture was then re-cooled to −78°C. and slowly poured on a stirred mixture of dry ice in diethyl ether.After stirring for 30 minutes, water was added to the reaction mixtureand the layers were separated after complete dissolution of solidmaterials. The aqueous layer was washed 2× with diethyl ether and thepH-value of the aqueous layer was adjusted to 5-6. The organic layer wasextracted 2× with MTB-ether. The combined organic layer was washed witha small amount of brine, dried over MgSO₄ and concentrated in vacuum.The residue was washed with hexane to remove oily by-products and driedin vacuum to afford 1.19 g of the title compound as beige solid. Theaqueous washing was concentrated on a rotary evaporator to approx. 50mL, inorganic salts were filtered off and MTB-ether was added to themother liquor. 6N hydrochloric acid was slowly added into thewell-stirred mixture until the pH-value was adjusted to −3. The layerswere separated, the aqueous layer was washed 2× with MTB-ether and 2×with chloroform. The combined organic layer was dried over MgSO₄ anddried in vacuum to give another 2.03 g of beige solid. Together, thefirst organic extract and 3.22 g of the title compound of the formula

were isolated as a beige solid. The compound was used in the next stepwithout further purification.

¹H-NMR (DMSO-D₆) δ (ppm): 1.47 (9H, s), 7.74 (1H, d, J=5 Hz), 8.34 (1H,d, J=5 Hz), 9.35 (1H, s), 10.07 (1H, s).

Step 3: Preparation of 3-aminoisonicotinic acid

3-tert-Butoxycarbonylamino-isonicotinic acid (450 mg) was dissolved inmethanol (8 mL) and 6N hydrochloric acid (5 mL) was added to thesolution. The resulting suspension was stirred under reflux for 2.5hours, cooled to room temperature and washed 3× with chloroform. Theaqueous layer was adjusted to pH-14 by addition of 2N sodium hydroxidesolution, washed 3× with chloroform and adjusted again to pH-3 byaddition of 2N hydrochloric acid. The aqueous layer was concentrated ona rotary evaporator to complete dryness and the residue was extractedwith hot ethanol. The ethanol extract was filtered to remove insolublematerial and concentrated in vacuum to afford 262 mg of the titlecompound of formula

as a yellow solid. The compound was used in the next step withoutfurther purification.

¹H-NMR (DMSO-D₆) δ (ppm): 7.78 (1H, d, J=5 Hz), 7.84 (1H, d, J=5 Hz),8.30 (1H, s).

Step 4: Preparation of 3-amino-2,6-dibromoisonicotinic acid

3-Aminoisonicotinic acid (260 mg) was dissolved in DMF (10 mL)N-bromosuccinimide (320 mg) was added and the reaction mixture wasstirred at room temperature for 1 hour before another portion ofN-bromosuccinimide (320 mg) was added. After stirring for 3 hours atroom temperature, the reaction mixture was quenched with water. 2NSodium hydroxide solution was added, the aqueous solution was washed 2×with diethyl ether and adjusted to pH-2 by addition of 6N hydrochloricacid. The aqueous layer was extracted 3× with MTB-ether, the combinedorganic layer was washed with brine, dried over MgSO₄ and concentratedin vacuum to afford 283 mg of the title compound of the formula

as a yellow-orange solid. The compound was contaminated with ca.10%impurities and was used without further purification in the next step.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.16 (2H, br s), 7.61 (1H, s).

Step 5: Preparation of6,8-dibromo-2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-pyrido[3,4-d][1,3]oxazin-4-one

A mixture of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid (example 1, step 5) (242 mg) and thionyl chloride (180 μl) wasstirred under reflux for 2 hours. Excess thionyl chloride wasco-evaporated with dry toluene on a evaporator, the residue re-dissolvedin dry acetonitrile (3 mL) and 3-amino-2,6-dibromoisonicotinic acid (282mg) was added. The solution was stirred for 10 minutes at roomtemperature and triethylamine (110 μL) was added and stirred for 20minutes, before a second portion of triethylamine (220 μL) was added.After the mixture was stirred for further 20 minutes at roomtemperature, methanesulfonyl chloride (75 μL) was added. After stirringfor 18 hours at room temperature, the reaction mixture was quenched byslow addition of water. The precipitate was filtered off, washed withwater/acetonitrile (1:2), acetonitrile and diethyl ether and dried invacuum to afford 153 mg of the title compound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.32 (1H, s), 7.50 (1H, dd, J=8 Hz, 5 Hz),8.00 (1H, d, J=8 Hz), 8.09 (1H, s), 8.56 (1H, d, J=5 Hz).

Step 6: Preparation ofN′-(2,6-dibromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-pyridine-4-carbonyl)-hydrazinecarboxylicacid methyl ester (5)

6,8-Dibromo-2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-pyrido[3,4-d][1,3]oxazin-4-one(153 mg) was dissolved in DMF (7 mL) and carbazaic acid methyl ester(240 mg) was added. The solution was stirred for 19 hours at roomtemperature. The reaction mixture was quenched with water and extractedwith MTB-ether. The organic layer was washed 3× with water, brine, driedover MgSO₄ and concentrated in vacuum. The residue was purified bycolumn chromatography (silica 60, chloroform/ethyl acetate=1:1,R_(f)=0.20) to afford 128 mg of compound 5 of the present invention ofthe formula

as a beige solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.49-3.62 (3H, m), 7.42 (1H, s), 7.61 (1H, dd,J=8 Hz, 5 Hz), 7.70 (1H, s), 8.17 (1H, d, J=8 Hz), 8.50 (1H, d, J=5 Hz),9.46 (1H, br s), 10.44 (1H, s), 10.75 (1H, s).

Example 6 Preparation ofN′-(4-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-pyridine-3-carbonyl)-hydrazinecarboxylicacid methyl ester (6) Step 1: Preparation of(3-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester

3-Chloro-isonicotinic acid (3.0 g) was dissolved in tert-butanol (80mL), diphenyl phosphoryl azide (5.24 g) and triethylamine (2.7 mL) wereadded and the reaction mixture was stirred at 100° C. for 5.5 h. Aftercooling to room temperature, the reaction mixture was concentrated invacuum and the residue was dissolved in ethyl acetate and water. Thelayers were separated and the aqueous layer was 2× extracted with ethylacetate, the combined organic layer was washed with brine, dried overmagnesium sulfate and concentrated in vacuum. The residue was purifiedby column chromatography (silica 60, hexane/ethyl acetate 3:1,R_(f)=0.30) to afford 2.74 g of the title compound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.55 (9H, s), 7.18 (1H, br s), 8.15 (1H, d,J=6 Hz), 8.36 (1H, d, J=6 Hz), 8.46 (1H, s).

Step 2: Preparation of 4-tert-butoxycarbonylamino-5-chloro-nicotinicacid

(3-Chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (1.50 g) wasdissolved in dry diethyl ether (35 mL),N,N,N′,N′-tertamethylenethylendiamine (2.35 mL) was added and thereaction mixture was cooled in a dry ice/acetone cool bath to −78° C.n-Butyl lithium (9.9 mL, 1.59M in hexane) was added to the suspension,the cool bath was replaced by a sodium chloride/ice mixture and thereaction mixture was stirred at −10° C. for 1.5 h. The suspension wasslowly poured on crushed dry ice (2.0 g) in dry diethyl ether (20 mL)and stirred for 1 h. Water was added and the pH was adjusted to −12 byaddition of 2N sodium hydroxide solution. The aqueous layer was washed2× with MTB-ether, 2 M hydrochloric acid was added to the aqueous layerand the pH was adjusted to −2 and the aqueous layer was 3× extractedwith ethyl acetate. The combined organic layer was washed with brine,dried over magnesium sulfate and concentrated in vacuum to afford 1.03 gof the title compound of the formula

as a beige solid. The crude product contained ˜30% valeric acid and wasused without further purification in the next step.

¹H-NMR (DMSO-D₆) δ (ppm): 1.44 (9H, s), 8.72 (1H, s), 8.74 (1H, s), 9.49(1H, s), 13.29 (1H, br s).

Step 3: Preparation of 4-amino-5-chloro-nicotinic acid

4-tert-Butoxycarbonylamino-5-chloro-nicotinic acid (1.03 g, crudeproduct from step 2 in a ˜3:1 mixture with valeric acid) was dissolvedin methanol (10 mL), 5 M hydrochloric acid (10 mL) was added and thereaction mixture was stirred for 1.5 h under gentle reflux. Aftercooling to room temperature, the mixture was concentrated in vacuum, theresidue was dissolved in water and the mixture was adjusted to pH ˜12 byaddition of 2N sodium hydroxide solution. The aqueous layer was washed2× with a mixture of MTB-ether/hexane (1:1), then 5 M hydrochloric acidwas added and the aqueous layer was adjusted to pH ˜2. The aqueous layerwas 2× washed with ethyl acetate and the aqueous layer was thenconcentrated in vacuum to dryness. The residue was 3× dissolved inmethanol/toluene and co-evaporated to dryness to remove traces of water.The residue was suspended in methanol (50 mL), stirred under reflux for30 min cooled to room temperature and insoluble salts were removed byfiltration. The filtrate was concentrated and dried in vacuum to afford1.59 g of a yellow solid containing the title compound of the formula

The crude product still contained inorganic salts and was used in thenext step without further purification.

¹H-NMR (DMSO-D₆) δ (ppm): 8.60-9.03 (2H, br m), 8.71 (1H, s), 8.73 (1H,s).

Step 4: Preparation of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-chloro-pyrido[4,3-d][1,3]oxazin-4-one

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (example1, step 5) (696 mg) was suspended in dry toluene (20 mL), oxalylchloride (580 μL) and 3 drops of dry DMF were added (gas evolution) andthe reaction mixture was stirred for 1 h at room temperature. Themixture was concentrated in vacuum and excess oxalyl chloride wasremoved by co-evaporation with dry toluene (3×). The residue wasdissolved in dry acetonitrile (20 mL) and 4-amino-5-chloro-nicotinicacid (crude mixture from the above step 3, 1.0 g) and triethylamine (320μL) were added. The reaction mixture was stirred for 30 minutes, beforea second portion of triethylamine (640 μL) was added. After the mixturewas stirred for further 20 minutes at room temperature, methanesulfonylchloride (195 μL) was added. After stirring for 4 h at room temperature,the reaction mixture was quenched by addition of water (10 mL). Theprecipitate was filtered off, washed with water/acetonitrile (1:2),acetonitrile and diethyl ether and dried in vacuum to afford 250 mg ofthe title compound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.36 (1H, s), 7.50 (1H, dd, J=8 Hz, 5 Hz),7.99 (1H, dd, J=8 Hz, 2 Hz), 8.55 (1H, dd, J=5 Hz, 2 Hz), 8.84 (1H, s),9.24 (1H, s).

Step 5: Preparation ofN′-(4-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-pyridine-3-carbonyl)-hydrazinecarboxylicacid methyl ester (6)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-chloro-pyrido[4,3-d][1,3]oxazin-4-one(150 mg) was dissolved in DMF (10 mL) and carbazaic acid methyl ester(154 mg) was added. The solution was stirred for 2 h at room temperaturebefore it was quenched with water. The mixture was 2× extracted withethyl acetate, the combined organic layer was 3× washed with water,washed with brine, dried over magnesium sulfate and concentrated invacuum. The residue was purified by column chromatography (silica 60,chloroform/methanol=10:1) to afford 99 mg of compound (6) of the presentinvention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.46-3.65 (3H, m), 7.45 (1H, s), 7.61 (1H, dd,J=8 Hz, 5 Hz), 8.17 (1H, d, J=8 Hz), 8.51 (1H, d, J=5 Hz), 8.64 (1H, s),8.86 (1H, s), 9.40 (1H, br s), 10.44 (1H, s), 10.81 (1H, s).

Example 7 Preparation of(N′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-hydrazinecarboxylicacid methyl ester (7) Step 1: Preparation of3-amino-6-chloro-2-iodo-4-methylpyridine

5-Amino-2-chloro-4-methylpyridine (1.35 g) was dissolved in DMF (20 mL),N-iodosuccinimide (2.59 g) was added and the reaction mixture wasstirred at room temperature for 12 hours. Ethyl acetate was added andthe organic layer was washed 3× with water, washed with brine, driedover MgSO₄ and concentrated in vacuum. The residue was purified bycolumn chromatography (silica 60, hexane/ethyl acetate=3:1, R_(f)=0.30)to afford 1.38 g of the title compound of the formula

as an orange solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.21 (3H, s), 4.06 (2H, br s), 6.95 (1H,s).

Step 2: Preparation of 3-amino-6-chloro-2-(2-furanyl)-4-methylpyridine

3-Amino-6-chloro-2-iodo-4-methylpyridine (1.38 g), 2-furanboronic acid(861 mg), and sodium carbonate (815 mg) were suspended in a solventmixture consistent of toluene (19 mL), THF (19 mL) and water (6 mL). Themixture was degassed using subsequent evaporation and flushing withnitrogen (5×) and tetrakis(triphenylphosphine)palladium(0) (658 mg) wasadded. The reaction mixture was stirred at 90° C. for 5 hours and 12hours at room temperature. After addition of another portion of2-furanboronic acid (430 mg) and tetrakis(triphenylphosphine)palladium(0) (132 mg), the mixture was stirred again for 12hours at 90° C. After 12 hours stirring at room temperature, thereaction mixture was quenched with water and extracted 2× with ethylacetate. The combined organic layer was washed with brine, dried overMgSO₄ and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate=4:1, R_(f)=0.25) toafford 929 mg of the title compound of the formula

as an orange solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.20 (3H, s), 4.65 (2H, br s), 6.56 (1H,dd, J=4 Hz, 2 Hz), 6.94 (1H, s), 7.07 (1H, dd, J=4 Hz, 1 Hz), 7.54 (1H,dd, J=2 Hz, 1 Hz).

Step 3: Preparation of 3-amino-6-chloro-4-methyl-pyridine-2-carboxylicacid

3-Amino-6-chloro-2-(2-furanyl)-4-methylpyridine (400 mg) was dissolvedin acetone (10 mL) and cooled in an ice bath to 0° C. A solutionprepared of potassium permanganate (909 mg) in water (15 mL) was addeddrop wise to this solution. After complete addition, the reactionmixture was allowed to warm to room temperature and stirred for 2 hours.The mixture was cooled again to 0° C. and a second portion of potassiumpermanganate (600 mg) in water (10 mL) was added and the cool bathremoved. After stirring for 2 hours, the reaction mixture was filteredthrough a pad of celite, the filter cake was washed carefully withwater, methanol and ethyl acetate and concentrated to approx. 10 mL on arotary evaporator. 2N Sodium hydroxide solution was added to adjust thepH-value to −12 and the aqueous layer was washed 2× with MTB-ether. Theaqueous layer was then adjusted to pH ˜2 by addition of 6N hydrochloricacid and extracted 3× with MTB-ether. The combined organic layer waswashed with brine, dried over MgSO₄ and concentrated in vacuum to afford262 mg of the title compound of the formula

as an orange-brown solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.24 (3H, d, J=1 Hz), 5.94 (2H, br s), 7.21(1H, d, J=1 Hz).

Step 4: Preparation of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one

A mixture of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid (example 1, step 5) (413 mg) and thionyl chloride (300 μl) wasstirred under reflux for 2 hours. Excess thionyl chloride wasco-evaporated with dry toluene on a evaporator, the residue re-dissolvedin dry acetonitrile (5 mL) and3-amino-6-chloro-4-methyl-pyridine-2-carboxylic acid (255 mg) was added.The solution was stirred for 15 minutes at room temperature andtriethylamine (190 μL) was added and stirred for 30 minutes, before asecond portion of triethylamine (380 μL) was added. After the mixturewas stirred for further 30 minutes at room temperature, methanesulfonylchloride (120 μL) was added. After stirring for 20 hours at roomtemperature, the reaction mixture was quenched by slow addition ofwater. The precipitate was filtered off, washed with water/acetonitrile(1:2), acetonitrile and diethyl ether and dried in vacuum to afford 112mg of the title compound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.89 (3H, d, J=1 Hz), 7.29 (1H, s), 7.47(1H, d, J=1 Hz), 7.50 (1H, dd, J=8 Hz, 5 Hz), 7.98 (1H, dd, J=8 Hz, 2Hz), 8.56 (1H, dd, J=5 Hz, 2 Hz).

Step 5: Preparation of(N′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-hydrazinecarboxylicacid methyl ester (7)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one(112 mg) was dissolved in DMF (7 mL) and carbazaic acid methyl ester(223 mg) was added. The solution was stirred for 3.5 hours, dried overMgSO₄ and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate=3:1, R_(f)=0.25) toafford 113 mg of compound 7 of the present invention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 2.19 (3H, s), 3.50-3.61 (3H, br m), 7.42 (1H,s), 7.62 (1H, dd, J=8 Hz, 5 Hz), 7.73 (1H, s), 8.18 (1H, dd, J=8 Hz, 2Hz), 8.50 (1H, dd, J=5 Hz, 2 Hz), 9.27 (1H, br s), 10.41 (1H, s), 10.56(1H, s).

Alternative preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-hydrazinecarboxylicacid methyl ester (7) Step 1: Preparation of(6-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester

6-Chloro-pyridin-3-ylamine (10.0 g) were dissolved in tert-butanol (140mL), di-tert-butyl dicarbonate (18.7 g) were added and the solution wasstirred at 50° C. for 4 h. Di-tert-butyl dicarbonate (3.40 g) was addedand the reaction mixture was stirred for another 8 h at 50° C. Most ofthe solvent was removed in vacuum and the residue was dissolved in ethylacetate and washed 3× with water, washed with brine, dried overmagnesium sulfate and concentrated in vacuum. The residue was purifiedby column chromatography (silica 60, chloroform/ethyl acetate 10:1,R_(f)=0.30) to afford 16.5 g of the title compound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.52 (9H, s), 6.54 (1H, br s), 7.27 (1H, d,J=3 Hz), 7.96 (1H, s), 8.23 (1H, d, J=3 Hz).

Step 2: Preparation of (6-chloro-4-methyl-pyridin-3-yl)-carbamic acidtert-butyl ester

(6-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (14.11 g) wasdissolved in dry diethyl ether (310 mL),N,N,N′,N′-tetramethyl-ethylene-1,2-diamine (23.1 mL) was added. Thesolution was cooled to −78° C., n-butyl lithium (97 mL, 1.59 M inhexane) was added, the cool bath replaced by an ice/sodium chloride coolbath and the suspension was stirred for 2 h at −10° C. The suspensionwas cooled again to −78° C. and methyl iodide (5.8 mL) was added slowly.The cool bath was removed and the reaction was quenched after 1 h byaddition of water. Ethyl acetate was added and the mixture wasneutralized by addition of 2 M hydrochloric acid. The layers wereseparated and the aqueous layer was extracted 2× with ethyl acetate, thecombined organic layer was washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate 5:1, R_(f)=0.10) toafford 4.24 g of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.52 (9H, s), 2.26 (3H, s), 6.21 (1H, s),7.13 (1H, s), 8.69 (1H, s).

Step 3: Preparation of (6-chloro-4-methyl-1-oxy-pyridin-3-yl)-carbamicacid tert-butyl ester

(6-Chloro-4-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (4.24 g)was dissolved in chloroform (40 mL), 3-chloroperoxybenzoic acid (5.87 g,77%) was added and the solution was stirred at room temperature for 21h. A second portion of 3-chloroperoxybenzoic acid (1.17 g) was added andthe reaction mixture was stirred for 5 h at room temperature. Chloroformwas added until complete dissolution of the solids and the organic phasewas washed with 2N sodium hydroxide solution. The aqueous washing was 1×re-extracted with chloroform and the combined organic layer was washedagain with 2N sodium hydroxide solution, water, brine, dried overmagnesium sulfate and concentrated in vacuum to afford 4.40 g of thetitle compound of the formula

as a white solid. The crude product was used without furtherpurification in the next step.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.52 (9H, s), 2.24 (3H, s), 6.24 (1H, s),7.22 (1H, s), 9.13 (1H, s).

Step 4: Preparation of (6-chloro-2-cyano-4-methyl-pyridin-3-yl)-carbamicacid tert-butyl ester

(6-Chloro-4-methyl-1-oxy-pyridin-3-yl)-carbamic acid tert-butyl ester(4.40 g) was suspended in dry acetonitrile (50 mL), trimethylsilylcyanide (7.2 mL) and triethyl amine (5.37 mL) were added and thereaction mixture was stirred under reflux for 2 h. After standing for 15h at room temperature, trimethylsilyl cyanide (4.4 mL) and triethylamine (3.65 mL) were added and the reaction mixture was stirred foranother 4 h at reflux. Water and 2N sodium hydroxide solution were addedafter cooling to room temperature and the mixture was 3× extracted withethyl acetate. The combined organic layer was washed with brine, driedover magnesium sulfate and concentrated in vacuum. The residue waspurified by column chromatography (silica 60, hexane/ethyl acetate=5:1,then 4:1, R_(f)=0.20 in hexane/ethyl acetate=4.1) to afford 3.72 g ofthe title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.52 (9H, s), 2.36 (3H, s), 6.43 (1H, s),7.42 (1H, s).

Step 5: Preparation of 3-amino-6-chloro-4-methyl-pyridine-2-carboxylicacid

(6-Chloro-2-cyano-4-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester(3.72 g) was dissolved in concentrated sulfuric acid (19 mL) and stirredfor 1 h at 100° C. The reaction mixture was cooled to room temperatureand water (19 mL) was slowly added. The reaction mixture was warmedagain to 100° C. and stirred at this temperature for 2 h. Water wasadded after cooling to room temperature, the mixture was cooled in anice bath and the pH was adjusted to ˜14 by slow addition of solid sodiumhydroxide. The aqueous solution was washed 2× with MTB-ether, theaqueous layer was then adjusted to pH ˜2 by addition of 5 M hydrochloricacid and extracted 3× with ethyl acetate. The combined organic layer waswashed with brine, dried over magnesium sulfate and concentrated invacuum to afford 2.25 g of the title compound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.24 (3H, s), 5.96 (2H, s), 7.20 (1H, s),10.69 (1H, br s).

Step 6: Preparation of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (example1, step 5) (3.65 g) was suspended in dry toluene (50 mL), oxalylchloride (3.10 mL) and 10 drops of dry DMF were added (gas evolution)and the reaction mixture was stirred for 1 h at room temperature. Themixture was concentrated in vacuum and excess oxalyl chloride wasremoved by co-evaporation with dry toluene (3×). The residue wasdissolved in dry acetonitrile (20 mL) and added to a suspension of3-amino-6-chloro-4-methyl-pyridine-2-carboxylic acid (2.25 g) inacetonitrile (30 mL). Triethylamine (1.7 mL)) was added and the reactionmixture was stirred for 20 minutes, before a second portion oftriethylamine (3.4 mL) was added. After the mixture was stirred forfurther 50 minutes at room temperature, methanesulfonyl chloride (1.03mL) was added. After stirring for 18 hours at room temperature, thereaction mixture was concentrated to −25 mL and water (20 mL) was added.The precipitate was filtered off, washed with water/acetonitrile (1:2),acetonitrile and diethyl ether and dried in vacuum to afford 3.97 g ofthe title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.89 (3H, d), 7.29 (1H, s), 7.47 (1H, s),7.50 (1H, dd, J=8 Hz, 5 Hz), 7.98 (1H, dd, J=8 Hz, 2 Hz), 8.56 (1H, dd,J=5 Hz, 2 Hz).

Step 7: Preparation of(N′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-hydrazinecarboxylicacid methyl ester (7)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one(500 mg) was dissolved in DMF (28 mL) acarbazaic acid methyl ester (994mg) was added. The solution was stirred for 3.5 h at room temperaturebefore it was quenched with water. The mixture was 2× extracted withethyl acetate, the combined organic layer was 3× washed with water,washed with brine, dried over magnesium sulfate and concentrated invacuum. The residue was purified by column chromatography (silica 60,chloroform/ethyl acetate=3:1, R_(f)=0.25) to afford 541 mg of thecompound (7) of the present invention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 2.19 (3H, s), 3.50-3.61 (3H, br m), 7.42 (1H,s), 7.62 (1H, dd, J=8 Hz, 5 Hz), 7.73 (1H, s), 8.18 (1H, dd, J=8 Hz, 2Hz), 8.50 (1H, dd, J=5 Hz, 2 Hz), 9.27 (1H, br s), 10.41 (1H, s), 10.56(1H, s).

Example 8 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N-methyl-hydrazinecarboxylicacid methyl ester (8) Step 1: Preparation ofN-methyl-hydrazine-carboxylic acid methyl ester

Monomethylhydrazine (10.6 mL) was dissolved in methanol (50 mL) andsodium hydroxide (8.0 g) was added. The suspension was cooled with anice bath and methyl chloroformate (15.4 mL) was added drop wise (violentreaction!), the ice bath was removed and the suspension was stirred for1 hour at room temperature. The white precipitate was filtered off,washed with methanol and the filtrate was concentrated in vacuum. Theresidue was purified by distillation (50-80° C./15 mmHg) to afford 13.4g of the title compound of the formula

as a colorless oil.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.11 (3H, s), 3.73 (3H, s), 4.13 (2H, brs).

Step 2: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N-methyl-hydrazinecarboxylicacid methyl ester (8)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one(140 mg) (example 7, step 4) was dissolved in DMF (10 mL) andN-methyl-hydrazinecarboxylic acid methyl ester (161 mg) was added. Thesolution was stirred for 3 hours at 80° C., then 12 hours at roomtemperature and again for 3.5 hours at 80° C. The reaction mixture wasquenched was diluted with MTB-ether and washed 4× with water, washedwith brine, dried over MgSO₄ and concentrated in vacuum. The residue waspurified by column chromatography (hexane/ethyl acetate=2:1, then 1.5:1,R_(f)=0.15 in hexane/ethyl acetate=2:1) to afford 112 mg of compound 8of the present invention of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.26 (3H, s), 3.28 (3H, s), 3.77 (3H, brs), 7.11 (1H, s), 7.35 (1H, s), 7.39 (1H, dd, J=8 Hz, 5 Hz), 7.86 (1H,dd, J=8 Hz, 2 Hz), 8.47 (1H, dd, J=5 Hz, 2 Hz), 9.58 (1H, s), 11.06 (1H,s).

Example 9 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N,N′-dimethyl-hydrazinecarboxylicacid methyl ester (9) Step 1: Preparation of5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid[6-chloro-2-(N,N′-dimethyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide

1,2-Dimethylhydrazine dihydrochloride (176 mg) and potassium carbonate(366 mg) were suspended in THF (8 mL) and 10 drops of water,2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one(example 7, step 4) (300 mg) was added and the reaction mixture wasstirred for 20 h at room temperature. Water and ethyl acetate wereadded, the layers were separated and the aqueous layer was 2× extractedwith ethyl acetate. The combined organic layer was washed with brine,dried over magnesium sulfate and concentrated in vacuum. The residue waspurified by column chromatography (silica 60, chloroform/ethylacetate=1:1, R_(f)=0.13) to afford 300 mg of the title compound of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.10 (1.5H, s), 2.13 (1.5H, s), 2.43 (1.5H,s), 2.66 (1.5H, s), 3.00 (1.5H, s), 3.23 (1.5H, s), 3.97 (0.5H, br s),5.52 (0.5H, br s), 7.04 (0.5H, s), 7.11 (0.5H, s), 7.26 (0.5H, s), 7.32(0.5H, s), 7.35-7.40 (1.0H, m), 7.82-7.87 (1.0H, m), 8.43-8.47 (1.0H,m), 10.07 (0.5H, s), 10.16 (0.5H, s).

Step 2: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N,N′-dimethyl-hydrazinecarboxylicacid methyl ester

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N,N′-dimethyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(250 mg) was dissolved in pyridine (3 mL), methyl chloroformate (150 μL)was added and the reaction mixture was stirred at room temperature.After 30 min, 1 h and 1.5 h, methyl chloroformate (each 75 μL) wasadded. After 1 h stirring at room temperature, the reaction mixture wasquenched with water and 3× co-evaporated with toluene. The residue wasdissolved in water and ethyl acetate, the layers were separated and theaqueous layer was extracted 2× with ethyl acetate. The combined organiclayer was washed with brine, dried over magnesium sulfate andconcentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate=1:1, R_(f)=0.20) toafford 223 mg of compound (9) of the present invention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 2.17 (1.5H, s), 2.24 (1.5H, s), 2.77 (1.5H,s), 2.84-2.85 (1.5H, m), 2.91-2.93 (1.5H, m), 3.09 (1.5H, s), 3.49(2.5H, s), 3.69 (0.5H, s), 7.35-7.39 (1.0H, m), 7.61-7.68 (2.0H, m),8.19-8.22 (1.0H, m), 8.49-8.52 (1.0H, m), 10.51-10.65 (1.0H, br m).

Example 10 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N-ethyl-hydrazinecarboxylicacid methyl ester (10) andN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N′-ethyl-hydrazinecarboxylic acid methyl ester (11) Step 1: Preparation of5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N′-ethyl-hydrazine carbonyl)-4-methyl-pyridin-3-yl]-amide(10-a) and 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid[6-chloro-2-(N-ethyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(11-a)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one(example 7, step 4) (600 mg) was suspended in THF (16 mL), and ethylhydrazine oxalate (398 mg) and potassium carbonate (732 mg) were addedand the reaction mixture was stirred for 19 h at room temperature. Waterand ethyl acetate were added and the layers were separated. The aqueouslayer was 1× extracted with ethyl acetate, the combined organic layerwere washed with brine, dried over magnesium sulfate and concentrated invacuum. The residue was purified by column chromatography (silica 60,chloroform/ethyl acetate 5:1, then 3:1, then 1:1, R_(f) (10-a)=0.45,R_(f) (11-a)=0.15 in chloroform/ethyl acetate=1:1) to afford 380 mg ofthe title compound (10-a) of the formula

as a white solid, and 228 mg of the title compound (11-a) of the formula

as a white solid.

(10-a): ¹H-NMR (CDCl₃, TMS) δ (ppm): 1.18 (3H, t, J=7 Hz), 2.25 (3H, s),2.99 (2H, q, J=7 Hz), 4.69 (1H, br s), 7.13 (1H, s), 7.29 (1H, s), 7.39(1H, dd, J=8 Hz, 5 Hz), 7.86 (1H, dd, J=8 Hz, 2 Hz), 8.48 (1H, dd, J=5Hz, 2 Hz), 9.18 (1H, br s), 11.45 (1H, s).

(11-a): ¹H-NMR (CDCl₃, TMS) δ (ppm): 1.09-1.19 (3.0H, m), 2.08 (1.7H,s), 2.11 (1.3H, s), 3.28 (0.8H, q, J=7 Hz), 3.63 (1.2H, q, J=7 Hz), 4.16(1.2H, s), 4.45 (0.8H, s), 7.01 (0.6H, s), 7.09 (0.4H, s), 7.31-7.33(1.0H, m), 7.35-7.41 (1.0H, m), 7.83-7.88 (1.0H, m), 8.43-8.48 (1.0H,m), 10.24 (0.4H, s), 10.56 (0.6H, s).

Step 2: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N-ethyl-hydrazinecarboxylicacid methyl ester (10)

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N′-ethyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(10-a) (320 mg) was dissolved in pyridine (4 mL), methyl chloroformate(190 μL) was added and the reaction mixture was stirred at roomtemperature. After 30 min, 1 h and 1.5 h, methyl chloroformate (each 95μL) was added. After 1 h stirring at room temperature, the reactionmixture was quenched with water and 3× co-evaporated with toluene. Theresidue was dissolved in water and ethyl acetate, the layers wereseparated and the aqueous layer was extracted 2× with ethyl acetate. Thecombined organic layer was washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate=2:1, R_(f)=0.10) toafford 308 mg of the title compound (10) of the present invention of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.22 (3H, t, J=7 Hz), 2.26 (3H, s), 3.69(2H, q, J=7 Hz), 3.76 (3H, s), 7.10 (1H, s), 7.35 (1H, s), 7.39 (1H, dd,J=8 Hz, 5 Hz), 7.86 (1H, dd, J=8 Hz, 2 Hz), 8.48 (1H, dd, J=5 Hz, 2 Hz),9.52 (1H, s), 11.09 (1H, s).

Step 3: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N′-ethyl-hydrazinecarboxylic acid methyl ester (11)

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N-ethyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(11-a) (177 mg) was dissolved in pyridine (2 mL), methyl chloroformate(100 μL) was added and the reaction mixture was stirred at roomtemperature. After 30 min, 1 h and 1.5 h, methyl chloroformate (each 50μL) was added. After 14 h stirring at room temperature, the reactionmixture was quenched with water and 3× co-evaporated with toluene. Theresidue was dissolved in water and ethyl acetate, the layers wereseparated and the aqueous layer was extracted 2× with ethyl acetate. Thecombined organic layer was washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate=3:1, R_(f)=0.10) toafford 135 mg of the title compound (11) of the present invention of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.14-1.27 (3H, m), 2.17 (3H, s), 3.62-3.80(5H, m), 7.12 (2H, s), 7.20-7.22 (1H, m), 7.39 (1H, dd, J=8 Hz, 5 Hz),7.87 (1H, dd, J=8 Hz), 8.46 (1H, d, J=5 Hz), 9.53 (1H, br s).

Example 11 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N-isopropyl-hydrazinecarboxylic acid methyl ester (12) andN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N′-isopropyl-hydrazinecarboxylicacid methyl ester (13) Step 1: Preparation of5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N′-isopropyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(12-a) and 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid[6-chloro-2-(N-isopropyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(13-a)

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one(example 7, step 4) (600 mg) was suspended in THF (16 mL), isopropylhydrazine (294 mg) was added and the reaction mixture was stirred for 19h at room temperature. Water and ethyl acetate were added and the layerswere separated. The aqueous layer was 1× extracted with ethyl acetate.The combined organic layers were washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate 2:1, then 1:1, R_(f)(12-a)=0.35, R_(f) (13-a)=0.15 in hexane/ethyl acetate=1:1) to afford478 mg of the title compound (12-a) of the formula

as a white solid, and 121 mg of the title compound (13-a) of the formula

as a white solid.

(12-a) ¹H-NMR (CDCl₃, TMS) δ (ppm): 1.14 (6H, d, J=6 Hz), 2.25 (3H, s),3.17-3.23 (1H, m), 4.63 (1H, s), 7.12 (1H, s), 7.29 (1H, s), 7.37-7.41(1H, m), 7.84-7.87 (1H, m), 8.46-8.48 (1H, m), 9.15 (1H, s), 11.46 (1H,s).

(13-a) ¹H-NMR (CDCl₃, TMS) δ (ppm): 1.09 (3.0H, d, J=7 Hz), 1.12 (3.0H,d, J=7 Hz), 2.08 (1.5H, s), 2.11 (1.5H, s), 3.75-3.80 (0.5H, m),3.80-4.16 (2.0H, br m), 4.69-4.75 (0.5H, m), 7.02 (0.5H, s), 7.09 (0.5H,s), 7.29 (0.5H, s), 7.31 (0.5H, s), 7.34-7.39 (1.0H, m), 7.82-7.86(1.0H, m), 8.41-8.46 (1.0H, m), 10.12 (0.5H, s), 10.42 (0.5H, s).

Step 2: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N-isopropyl-hydrazinecarboxylic acid methyl ester (12)

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N′-isopropyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(12-a) (378 mg) was dissolved in pyridine (5 mL), methyl chloroformate(220 μL) was added and the reaction mixture was stirred at roomtemperature. After 30 min, 1 h and 1.5 h, methyl chloroformate (each 110μL) was added. After 18 h stirring at room temperature, the reactionmixture was quenched with water and 3× co-evaporated with toluene. Theresidue was dissolved in water and ethyl acetate, the layers wereseparated and the aqueous layer was extracted 2× with ethyl acetate. Thecombined organic layer was washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate=10:1, R_(f)=0.13) toafford 382 mg of the title compound (12) of the present invention of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.20 (6H, d, J=7 Hz), 2.26 (3H, s), 3.75(3H, s), 4.54-4.60 (1H, m), 7.09 (1H, s), 7.36 (1H, s), 7.39 (1H, dd,J=8 Hz, 5 Hz), 7.85 (1H, dd, J=8 Hz, 2 Hz), 8.48 (1H, dd, J=5 Hz, 2 Hz),9.28 (1H, s), 11.12 (1H, s).

Step 3:N′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-4-methyl-pyridine-2-carbonyl)-N′-isopropyl-hydrazinecarboxylicacid methyl ester (13)

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[6-chloro-2-(N-isopropyl-hydrazinocarbonyl)-4-methyl-pyridin-3-yl]-amide(13-a) (121 mg) was dissolved in pyridine (2 mL), methyl chloroformate(70 μL) was added and the reaction mixture was stirred at 50° C. After 1h, methyl chloroformate (each 40 μL) was added 8× in a time interval of30 min at 50° C. After 10 h stirring at room temperature, the reactionmixture was quenched with water and 3× co-evaporated with toluene. Theresidue was dissolved in water and ethyl acetate, the layers wereseparated and the aqueous layer was extracted 2× with ethyl acetate. Thecombined organic layer was washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate=3:1, R_(f)=0.15) toafford 67 mg of the title compound (13) of the present invention of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.00-1.30 (6H, m), 2.14 (3H, s), 3.57-3.81(3H, br m), 4.62-4.79 (1H, m), 6.96-7.18 (3H, m), 7.39 (1H, dd, J=8 Hz,5 Hz), 7.86 (1H, dd, J=8 Hz), 8.45 (1H, d, J=5 Hz), 9.66-9.86 (1H, m).

Example 12 Preparation ofN″-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-4,6-dichloro-pyridine-2-carbonyl)-hydrazinecarboxylicacid methyl ester (14) Step 1: Preparation of 2-chloro-pyridin-3-ylamine

3-Aminopyridine (25.0 g) was dissolved in concentrated hydrochloric acid(250 mL, 37%) at 30 to 35° C. and cooled in an ice bath after completedissolution of the starting material. Hydrogen peroxide (28.5 mL, 30%aqueous solution) was added slowly with a dropping funnel to thesolution in a rate that the temperature was kept below 10° C. over aperiod of 30 min. The orange solution was slowly warmed up to roomtemperature over a time period of 2 h and stirred at room temperaturefor another 2 h. The solution was cooled in an ice bath and 160 mL of anaqueous sodium hydroxide solution (50%) were added slowly. The acidicaqueous solution was washed with 30 mL toluene and the organic washingwas re-extracted 1× with 5N aqueous hydrochloric acid. Aqueous sodiumhydroxide solution (50%) was added to the combined acidic aqueoussolution and the pH was adjusted to ˜8-10. The aqueous solution was 3×extracted with 200 mL toluene, the combined organic layer was washedwith brine, dried over magnesium sulfate and concentrated in vacuum. Theresidue was purified by column chromatography (silica 60,chloroform/ethyl acetate 20:1, R_(f)=0.25) to afford 17.6 g of the titlecompound of the formula

as an orange solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 4.12 (2H, br s), 7.04-7.05 (2H, m),7.78-7.81 (1H, m).

Step 2: Preparation of 3-amino-pyridine-2-carbonitrile

2-Chloro-pyridin-3-ylamine (2.0 g) was dissolved in DMF (24 mL) and zinccyanide (1.83 g) was added to the solution. The solution was degassed invacuum 5×, tetrakis(triphenylphosphine) palladium(0) (901 mg) was addedand the reaction mixture was stirred at 90° C. for 7 h. After thereaction mixture was cooled to room temperature, the solid was removedby filtration and the filter cake was washed with ethyl acetate. Waterwas added to the filtrate, the layers were separated and the aqueouslayer was 2× extracted with ethyl acetate. The combined organic layerwas washed 3× with water, washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate 3:1, R_(f)=0.25) toafford 755 mg of the title compound of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 4.43 (2H, br s), 7.10 (1H, dd, J=9 Hz, 1Hz), 7.25-7.29 (1H, m), 8.07 (1H, dd, J=4 Hz, 1 Hz).

Step 3: Preparation of 3-amino-4,6-dichloro-pyridine-2-carbonitrile

3-Amino-pyridine-2-carbonitrile (100 mg) was dissolved in DMF (2 mL) andN-chorosuccinimide (246 mg) was added. The solution was stirred for 20 hat room temperature before water was added. The mixture was 2× extractedwith ethyl acetate, the combined organic layer was washed 3× with water,washed with brine, dried over magnesium sulfate and concentrated invacuum. The residue was purified by column chromatography (silica 60,hexane/ethyl acetate=3:1, R_(f)=0.30) to afford 121 mg of the titlecompound of the formula

as an orange solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 4.92 (2H, br s), 7.44 (1H, s).

Step 4: Preparation of 3-amino-4,6-dichloro-pyridine-2-carboxylic acid

3-Amino-4,6-dichloro-pyridine-2-carbonitrile (121 mg) was dissolved inconcentrated sulfuric acid (1 mL) and stirred for 1 h at 100° C. Thereaction mixture was cooled to room temperature and water (1 mL) wasslowly added. The reaction mixture was warmed again to 100° C. andstirred at this temperature for 2 h. Water was added after cooling toroom temperature, the pH was adjusted to ˜10 by addition of solid sodiumbicarbonate and the aqueous solution was washed 2× with MTB-ether. Theaqueous layer was then adjusted to pH ˜2 by addition of 2 M hydrochloricacid and extracted 3× with ethyl acetate. The combined organic layer waswashed with brine, dried over magnesium sulfate and concentrated invacuum to afford 99 mg of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.37 (2H, br s), 7.47 (1H, s), 10.50 (1H,br s).

Step 5: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-4,6-dichloro-pyridine-2-carbonyl)-hydrazinecarboxylicacid methyl ester

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (example1, step 5) (142 mg) was suspended in acetonitrile (1 mL) and pyridine(65 μL) and methanesulfonyl chloride (50 μL) were added. The reactionmixture was stirred for 30 min at room temperature,3-amino-4,6-dichloro-pyridine-2-carboxylic acid (99 mg) in acetonitrile(1 mL) and pyridine (130 μL) were added and the reaction mixture wasstirred 1 h at room temperature. Methanesulfonyl chloride (65 μL) wasadded and the reaction mixture was stirred for 20 h at room temperature.The reaction mixture was concentrated in vacuum, the residue wassuspended in DMF (5 mL), carbazaic acid methyl ester (216 mg) was addedand the reaction mixture was stirred for 20 h at room temperature. Waterwas added and the mixture was 2× extracted with MTB-ether. The combinedorganic layer was washed 3× with water, washed with brine, dried overmagnesium sulfate and concentrated in vacuum. The residue was purifiedby column chromatography (silica 60, hexane/ethyl acetate=2:1,R_(f)=0.15) to afford 37 mg of the compound 14 of the present inventionof the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.82 (3H, s), 6.66 (1H, br s), 7.08 (1H,s), 7.39 (1H, dd, J=8 Hz, 5 Hz), 7.57 (1H, s), 7.86 (1H, dd, J=8 Hz, 2Hz), 8.47 (1H, dd, J=5 Hz, 2 Hz), 9.40 (1H, s), 10.71 (1H, s).

Example 13 Preparation ofN′-(4-bromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-pyridine-2-carbonyl)-hydrazinecarboxylic acid methyl ester (15) Step 1: Preparation of3-amino-6-chloro-2-iodopyridine

5-Amino-2-chloropyridine (3.0 g) was dissolved in DMF (40 mL),N-iodosuccinimide (5.25 g) was added and the reaction mixture wasstirred at room temperature for 3 hours. Water and MTB-ether were addedto the reaction mixture, the layers were separated and the organic layerwas washed 3× with water, washed with brine, dried over MgSO₄ andconcentrated in vacuum. The residue was purified by columnchromatography (silica 60, hexane/ethyl acetate=3:1, R_(f)=0.30) toafford 4.80 g of the title compound of the formula

as an orange solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 4.13 (2H, br s), 6.89 (1H, d, J=8 Hz), 7.05(1H, d, J=8 Hz).

Step 2: Preparation of 3-amino-6-chloro-2-(2-furanyl)pyridine

3-Amino-6-chloro-2-iodopyridine (1.78 g), 2-furanboronic acid (1.17 g),and sodium carbonate (1.11 g) were suspended in a solvent mixtureconsistent of toluene (23 mL), THF (23 mL) and water (7 mL). The mixturewas degassed using subsequent evaporation and flushing with nitrogen(5×) and tetrakis(triphenylphosphine)palladium(0) (808 mg) was added.The reaction mixture was stirred at 90° C. for 7 hours and 14 hours atroom temperature. After addition of 2-furanboronic acid (783 mg), themixture was stirred again for 4 hours at 90° C., then another portion of2-furanboronic acid (390 mg) was added and the reaction mixture wasstirred for 5.5 hours at 90° C. After 15 hours stirring at roomtemperature, the reaction mixture was quenched with water and extracted2× with ethyl acetate. The combined organic layer was washed with brine,dried over MgSO₄ and concentrated in vacuum. The residue was purified bycolumn chromatography (silica 60, hexane/ethyl acetate=3:1, R_(f)=0.25)to afford 1.26 mg of the title compound of the formula

as a beige solid. The compound contained ˜10%3-amino-6-chloro-2-iodopyridine and was used without furtherpurification in the next step.

¹H-NMR (CDCl₃, TMS) δ (ppm): 4.65 (2H, br s), 6.56 (1H, dd, J=4 Hz, 2Hz), 6.99 (2H, s), 7.08 (1H, d, J=4 Hz), 7.54 (1H, d, J=2 Hz).

Step 3: Preparation of 3-amino-6-chloro-pyridine-2-carboxylic acid

3-Amino-6-chloro-2-(2-furanyl)pyridine (1.06 g) was dissolved in acetone(25 mL) and cooled in an ice bath to 0° C. A solution prepared ofpotassium permanganate (2.57 g) in water (40 mL) was added drop wise tothis solution. After complete addition, the reaction mixture was allowedto warm to room temperature and stirred for hours. The mixture wascooled again to 0° C. and a second portion of potassium permanganate(858 mg) in water (15 mL) was added and the cool bath removed. Afterstirring for 2 hours, the reaction mixture was filtered through a pad ofcelite, the filter cake was washed carefully with water, methanol andethyl acetate and concentrated to approx. 20 mL on a rotary evaporator.2N Sodium hydroxide solution was added to adjust the pH-value to −12 andthe aqueous layer was washed 2× with MTB-ether. The aqueous layer wasadjusted to pH ˜2 by addition of 6N hydrochloric acid and extracted 3×with MTB-ether. The combined organic layer was washed with brine, driedover MgSO₄ and concentrated in vacuum to afford 636 mg of the titlecompound of the formula

as a brown solid. The compound still contained ˜30% of an unknownimpurity and was used in the next step without further purification.

¹H-NMR (DMSO-D₆) δ (ppm): 7.28 (1H, d, J=9 Hz), 7.34 (1H, d, J=9 Hz).

Step 4: Preperation of 3-amino-6-chloro-pyridine-2-carboxylic acidmethyl ester

3-Amino-6-chloro-pyridine-2-carboxylic acid (636 mg) was suspended inmethanol (8 mL) and toluene (22 mL) was added. A solution of(trimethylsilyl)diazomethane (2.0 M in hexane, 2.4 mL) was added slowlyto the reaction mixture. After 1 hour stirring at room temperature,another portion of (trimethylsilyl)diazomethane (550 μl) was added andthe mixture was stirred for additional 45 minutes. The reaction mixturewas quenched with water and extracted 3× with ethyl acetate. Thecombined organic layer was washed with 2N hydrochloric acid, saturatedbicarbonate solution and brine, dried over MgSO₄ and concentrated invacuum. The residue was purified by column chromatography (silica gel60, choroform/ethyl acetate=50:1, R_(f)=0.30) to afford 365 mg of thetitle compound of the formula

as a yellow solid. The compound still contained ˜30% of an unknownimpurity and was used in the next step without further purification.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.96 (3H, s), 5.82 (2H, br s), 7.05 (1H, d,J=9 Hz), 7.23 (1H, d, J=9 Hz).

Step 5: Preparation of 3-amino-4-bromo-6-chloro-pyridine-2-carboxylicacid methyl ester

3-Amino-6-chloro-pyridine-2-carboxylic acid methyl ester (365 mg) wasdissolved in DMF (10 mL) and N-bomosuccinimide (418 mg) was added. Thesolution was stirred at 50° C. for 5 hours and diluted with MTB-ether.The organic layer was washed 4× with water, washed with brine, driedover MgSO₄ and concentrated in vacuum. The residue was purified bycolumn chromatography (silica 60, hexane/ethyl acetate=5:1, R_(f)=0.25)to afford 169 mg of 3-amino-4-bromo-6-chloro-2-picolinic acid methylester

as an orange solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 3.97 (3H, s), 6.39 (2H, br s), 7.58 (1H,s).

Step 6: Preparation of 3-amino-4-bromo-6-chloro-pyridine-2-carboxylicacid

3-Amino-4-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (169mg) was suspended in methanol (3 mL) and 2N sodium hydroxide solution (2mL). The suspension was stirred at 50° C. for 3 hours. The precipitatewas filtered off and washed carefully with diethyl ether. Theprecipitate was dissolved in a mixture of 2N hydrochloric acid and ethylacetate and the layers were separated. The aqueous layer was 2×extracted with ethyl acetate, washed with brine, dried over MgSO₄ andconcentrated in vacuum to afford 138 mg of the title compound of theformula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.46 (2H, br s), 7.63 (1H, s), 10.59 (1H,br s).

Step 7: Preparation of8-bromo-2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-pyrido[3,2-d][1,3]oxazin-4-one

A mixture of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid (example 1, step 5) (183 mg) and thionyl chloride (130 μl) wasstirred under reflux for 2 hours. Excess thionyl chloride wasco-evaporated with dry toluene on a evaporator, the residue re-dissolvedin dry acetonitrile (3 mL) and3-amino-4-bromo-6-chloro-pyridine-2-carboxylic acid (138 mg) was added.The solution was stirred for 15 minutes at room temperature andtriethylamine (85 μL) was added and stirred for 30 minutes, before asecond portion of triethylamine (170 μL) was added. After the mixturewas stirred for further 30 minutes at room temperature, methanesulfonylchloride (55 μL) was added. After stirring for 21 hours at roomtemperature, the reaction mixture was quenched by slow addition ofwater. The precipitate was filtered off, washed with water/acetonitrile(1:2), acetonitrile and diethyl ether and dried in vacuum to afford 141mg of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.33 (1H, s), 7.48 (1H, dd, J=8 Hz, 5 Hz),7.88 (1H, s), 7.98 (1H, dd, J=8 Hz, 2 Hz), 8.55 (1H, dd, J=5 Hz, 2 Hz).

Step 8: Preparation ofN′-(4-bromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-6-chloro-pyridine-2-carbonyl)-hydrazinecarboxylic acid methyl ester (15)

8-Bromo-2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-pyrido[3,2-d][1,3]oxazin-4-one(141 mg) was dissolved in DMF (8 mL) and carbazaic acid methyl ester(243 mg) was added. The solution was stirred for 14 hours at roomtemperature. The reaction mixture was diluted with MTB-ether and theorganic layer was washed 4× with water, brine, dried over MgSO₄ andconcentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate=3:1, R_(f)=0.20) toafford 120 mg of compound 15 of the present invention of the formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.46-3.62 (3H, br m), 7.45 (1H, s), 7.61 (1H,dd, J=8 Hz, 5 Hz), 8.16 (1H, dd, J=8 Hz, 2 Hz), 8.28 (1H, s), 8.50 (1H,dd, J=5 Hz, 2 Hz), 9.31 (1H, br s), 10.45 (1H, s), 10.72 (1H, s).

Example 14 Preparation ofN′-(4,6-dibromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-pyridine-2-carbonyl)-N′-ethyl-hydrazinecarboxylicacid methyl ester (16) Step 1: Preparation ofN′-ethylidene-hydrazinecarboxylic acid methyl ester

Carbazaic acid methyl ester (10 g) was suspended in toluene (60 mL) andwarmed up to 50° C. for 10 min. The flask was equipped with a droppingfunnel, filled with a solution of acetaldehyde (5.86 g) in toluene (20mL) and the solution was slowly dropped to the suspension within 10 min.The mixture was stirred for 1 h at 50° C., and then cooled to roomtemperature. The product started crystallizing and cooling in an icebath completed the crystallizing process. The white crystals werefiltered off, washed with small amounts of cold toluene and dried invacuum to give 12.07 g of the title compound of the formula

as white crystals (mainly one diastereomer).

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.99 (3H, d, J=5 Hz), 3.82 (3H, br s), 7.24(1H, q, J=5 Hz), 8.06-8.56 (1H, br m).

Step 2: Preparation of N′-ethyl-hydrazinecarboxylic acid methyl ester

N′-Ethylidene-hydrazinecarboxylic acid methyl ester (5.0 g) wasdissolved in of dry THF (50 mL) and stirred at 50° C. Sodium borohydride(1.95 g) (gas evolution) and dry methanol (4.2 mL) were added. Thesuspension turned into a solution within 5 to 10 min and the gasevolution ceased within 30 min. The solution was stirred for 3 h at 50°C., before 50 mL dry methanol was added and the solution was stirredunder reflux for 2 h. The solvent was removed on an evaporator and theresidue was treated with 20 mL of chloroform and stirred for 10 min at50° C., before it was filtered over a pad of celite and was washed 3×with 30 mL of chloroform. The filtrate was concentrated in vacuum andthe residue was purified by column chromatography (silica 60,chloroform/ethyl acetate=3:1; R_(f)=0.20) to afford 3.70 g of the titlecompound of the formula

as a colorless oil.

¹H-NMR (DMSO-D₆) δ (ppm): 0.93 (3H, t, J=7 Hz), 2.66-2.73 (2H, m), 3.54(3H, s), 4.39-4.42 (1H, m), 8.45 (1H, br s).

Step 3: Preparation of 3-amino-4,6-dibromo-pyridine-2-carbo nitrile

2-Chloro-pyridin-3-ylamine (100 mg) was dissolved in DMF (2 mL) andN-bromosuccinimide (329 mg) was added. The solution was stirred for 26 hat room temperature before water was added. The mixture was 2× extractedwith ethyl acetate, the combined organic layer was washed 3× with water,washed with brine, dried over magnesium sulfate and concentrated invacuum. The residue was purified by column chromatography (silica 60,hexane/ethyl acetate=3:1, R_(f)=0.30) to afford 158 mg of the titlecompound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 4.93 (2H, s), 7.72 (1H, s).

Step 4: Preparation of 3-amino-4,6-dibromo-pyridine-2-carboxylic acid

3-amino-4,6-dibromo-pyridine-2-carbonitrile (158 mg) was dissolved inconcentrated sulfuric acid (1.5 mL) and stirred for 1 h at 100° C. Thereaction mixture was cooled to room temperature and water (1.5 mL) wasslowly added. The reaction mixture was warmed again to 100° C. andstirred at this temperature for 2 h. Water was added after cooling toroom temperature, the pH was adjusted to −10 by addition of solid sodiumbicarbonate and the aqueous solution was washed 2× with MTB-ether. Theaqueous layer was then adjusted to pH ˜2 by addition of 2 M hydrochloricacid and extracted 3× with ethyl acetate. The combined organic layer waswashed with brine, dried over magnesium sulfate and concentrated invacuum to afford 123 mg of the title compound of the formula

as a yellow solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 6.43 (2H, br s), 7.75 (1H, s), 10.53 (1H,br s).

Step 5: Preparation ofN′-(4,6-dibromo-3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-pyridine-2-carbonyl)-N′-ethyl-hydrazinecarboxylicacid methyl ester (16)

5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (example1, step 5) (126 mg) was suspended in acetonitrile (1 mL) and pyridine(55 μL) and methanesulfonyl chloride (40 μL) were added. The reactionmixture was stirred for 30 min at room temperature,3-amino-4,6-dibromo-pyridine-2-carboxylic acid (123 mg) in acetonitrile(1 mL) and pyridine (115 μL) was added and the reaction mixture wasstirred 1 h at room temperature. Methanesulfonyl chloride (40 μL) wasadded and the reaction mixture was stirred for 13 h at room temperature.The reaction mixture was concentrated in vacuum, the residue wassuspended in NMP (1 mL), N′-ethyl-hydrazinecarboxylic acid methyl ester(237 mg, step 2) was added and the reaction mixture was stirred for 1 hat 80° C. Water was added after cooling to room temperature and themixture was 2× extracted with ethyl acetate. The combined organic layerwas washed 4× with water, washed with brine, dried over magnesiumsulfate and concentrated in vacuum. The residue was purified by columnchromatography (silica 60, chloroform/ethyl acetate=10:1, then 5:1, then3:1, R_(f)=0.25 in chloroform/ethyl acetate=3:1) to afford 90 mg of awhite solid. The compound was purified again by column chromatography(silica 60, hexane/ethyl acetate=1:1, R_(f)=0.20) to afford 60 mg ofcompound 16 of the present invention of the formula

as a white solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.02-1.16 (3.0H, m), 3.67-3.90 (5.0H, m),6.98 (0.5H, s), 7.18 (1.5H, s), 7.41 (1.0H, dd, J=8 Hz, 5 Hz), 7.68(1.0H, s), 7.88 (1.0H, dd, J=8 Hz, 2 Hz), 8.47 (1.0H, dd, J=5 Hz, 2 Hz),9.32-9.53 (1.0H, m).

Example 15 Preparation ofN′-(2-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-pyridine-3-carbonyl)-hydrazinecarboxylicacid methyl ester (17) Step 1: Preparation of2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[2,3-d][1,3]oxazin-4-one

5-Trifluoromethyl-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylicacid chloride (example 2, step 3) (800 mg) was added to a mixture of2-aminonicotinic acid (356 mg) in acetonitrile (20 mL). The mixture wasstirred for 10 minutes at room temperature and triethylamine (360 μL)was added and stirred for 15 minutes, before a second portion oftriethylamine (720 μL) was added. After the mixture was stirred forfurther 15 minutes at room temperature, methanesulfonyl chloride (220μL) was added. After stirring for 1.5 hours at room temperature, thereaction was quenched with water and extracted 2× with ethyl acetate,washed with brine, dried over MgSO₄ and concentrated in vacuum. Theresidue was purified by column chromatography (silica 60,chloroform/ethyl acetate=1:1, R_(f)=0.40) to afford 660 mg of the titlecompound of the formula

as a beige solid.

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.49 (1H, dd, J=8 Hz, 5 Hz), 7.56 (1H, dd,J=8 Hz, 5 Hz), 7.62 (1H, s), 8.02 (1H, dd, J=8 Hz, 2 Hz), 8.50 (1H, dd,J=8 Hz, 2 Hz), 8.56 (1H, dd, J=5 Hz, 2 Hz), 8.94 (1H, dd, J=5 Hz, 2 Hz).

Step 2: Preparation ofN′-(2-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-pyridine-3-carbonyl)-hydrazinecarboxylicacid methyl ester (17)

2-[2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[2,3-d][1,3]oxazin-4-one(292 mg) was dissolved in DMF (18 mL), carbazaic acid methyl ester (667mg) was added and the solution was stirred for 16 hours at roomtemperature. The reaction mixture was quenched with water and extractedwith MTB-ether. The organic layer was washed 3× with water, washed withbrine, dried over MgSO₄ and concentrated in vacuum. The residue waspurified by column chromatography (silica 60, chloroform/methanol=20:1,R_(f)=0.15) to afford 157 mg of compound 17 of the present invention ofthe formula

as a white solid.

¹H-NMR (DMSO-D₆) δ (ppm): 3.48-3.64 (3H, br m), 7.38 (1H, br s),7.67-7.69 (2H, m), 8.07 (1H, br s), 8.24 (1H, dd, J=8 Hz, 1 Hz),8.52-8.56 (2H, m), 9.31 (1H, br s), 10.43 (1H, br s), 11.48 (1H, br s).

Example 16 Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-4-methyl-thiophene-2-carbonyl)-hydrazinecarboxylicacid methyl ester (18) Step 1: Preparation of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-7-methyl-thieno[3,2-d][1,3]oxazin-4-one

A mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylicacid (example 1, step 5) (600 mg) and thionyl chloride (2 ml) was heatedto reflux for 2 hours. The reaction mixture was allowed to cool to roomtemperature and concentrated under reduced pressure. The resultingresidue was dissolved in acetonitrile (10 mL) and3-amino-4-methyl-thiophene-2-carboxylic acid (310 mg) was added. Themixture was stirred at room temperature for 30 minutes. Then,triethylamine (200 mg) was added to the mixture. After stirring themixture at room temperature for 30 minutes, a second portion oftriethylamine (400 mg) was added and the mixture was stirred at roomtemperature for 30 minutes. Methanesulfonyl chloride (500 mg) was addedand the mixture was stirred at room temperature for 6 hours. Water waspoured into the reaction mixture and the mixture was concentrated underreduced pressure. The resulting residue was washed with water andMTB-ether to afford 0.72 g of the title compound of the formula

¹H-NMR (DMSO-D₆) δ (ppm): 1.74 (3H, br s), 7.52-7.57 (1H, m), 7.74-7.80(1H, m), 8.02 (1H, br s), 8.30-8.37 (1H, m), 8.60-8.64 (1H, m).

Step 2: Preparation ofN′-(3-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-4-methyl-thiophene-2-carbonyl)-hydrazinecarboxylicacid methyl ester (18)

A mixture of2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-7-methyl-thieno[3,2-d][1,3]oxazin-4-one(210 mg), carbazaic acid methyl ester (450 mg) and DMF (10 mL) wasstirred at room temperature for 10 hours. The reaction mixture wasquenched with water and the mixture was extracted with ethyl acetate.The organic layer was washed with water, dried over sodium sulfate andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel column chromatography to afford 120 mg of compound 18 ofthe present invention of the formula

¹H-NMR (DMSO-D₆) δ (ppm): 1.96-2.01 (3H, m), 3.58-3.65 (3H, m),7.38-7.47 (2H, m), 7.62 (1H, dd, J=8 Hz, 5 Hz), 8.16-8.23 (1H, m), 8.50(1H, d, J=4 Hz), 9.24 (1H, br s), 9.83 (1H, br s), 10.28 (1H, br s)

Example 17 Preparation ofN′-(5-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-1-methyl-1H-pyrazole-4-carbonyl)-hydrazinecarboxylicacid methyl ester (19) Step 1: Preparation of6-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-1-methyl-1H-pyrazolo[3,4-d][1,3]oxazin-4-one

A mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylicacid (example 1, step 5) (1.10 g) and thionyl chloride (4 mL) was heatedto reflux for 2 hours. The reaction mixture was allowed to cool to roomtemperature, and concentrated under reduced pressure. The resultingresidue was dissolved in acetonitrile (10 mL) and of5-amino-1-methyl-1H-pyrazole-4-carboxylic acid (520 mg) was added. Themixture was stirred at room temperature for 30 minutes. Then,triethylamine (400 mg) was added to the mixture. After stirring at roomtemperature for 30 minutes, a second portion of triethylamine (800 mg)was added and the mixture was stirred at room temperature for 30minutes.

Methanesulfonyl chloride (600 mg) of was added, and the mixture wasstirred at room temperature for 6 hours. Water was poured into thereaction mixture and the mixture was concentrated under reducedpressure. The resulting residue was washed with water and MTB-ether toafford 900 mg of the title compound of the formula

¹H-NMR (DMSO-D₆) δ (ppm): 3.46 (3H, s), 7.60 (1H, s), 7.78 (1H, dd, J=8Hz, 5 Hz), 8.24 (1H, s), 8.35 (1H, d, J=8 Hz), 8.63 (1H, d, J=5 Hz).

Step 2: Preparation ofN′-(5-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-1-methyl-1H-pyrazole-4-carbonyl)-hydrazinecarboxylicacid methyl ester (19)

A mixture of6-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d][1,3]oxazin-4-one(300 mg), carbazaic acid methyl ester (700 mg) and DMF (10 mL) wasstirred at room temperature for 10 hours. The reaction mixture wasquenched with water and the mixture was extracted with ethyl acetate.The organic layer was washed with water, dried over sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel column chromatography to afford 200 mg of compound 19 ofthe present invention of the formula

¹H-NMR (DMSO-D₆) δ (ppm): 3.55-3.60 (6H, m), 7.48 (1H, s), 7.64 (1H, dd,J=8 Hz, 5 Hz), 7.96 (1H, s), 8.20 (1H, d, J=8 Hz), 8.52 (1H, d, J=5 Hz),9.08 (1H, br s), 9.86 (1H, br s), 10.79 (1H, br s).

Example 18 Preparation ofN′-(6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2-trifluoromethyl-quinoline-7-carbonyl)-hydrazinecarboxylicacid methyl ester (20) Step 1: Preparation of5-oxo-2-trifluoromethyl-5,6,7,8-tetra hydro-quinoline-7-carboxylic acidmethyl ester

A solution of 3,5-dioxo-cyclohexanecarboxylic acid methyl ester (3.6 g,preparation as described in J. Chem. Soc., Perkin Trans. 1 (1976), (13),1382-4), (Z)-amino-1,1,1-trifluoro-but-3-en-2-one (2.94 g, prepared asdescribed in EP 744400 (1996)), trifluoroacetic acid (1.21 g) andammonium trifluoroacetate (1.39 g) in toluene (50 mL) are heated atreflux temperature in a Dean-Stark apparatus. After reaction completion,the reaction mixture is cooled, diluted with ethyl acetate and washedsuccessively with saturated aqueous sodium bicarbonate and water. Theorganic phase is dried over anhydrous sodium sulfate, filtered andconcentrated in vacuum. The residue is purified by column chromatography(eluting with hexane/ethyl acetate=4:1) to give 1.5 g of the titlecompound of the formula

as white crystals.

Step 2: Preparation of5-hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

A solution of5-oxo-2-trifluoromethyl-5,6,7,8-tetrahydro-quinoline-7-carboxylic acidmethyl ester (50.0 g) is dissolved in methylene chloride (500 mL) andtreated drop wise with a solution of bromotrichloromethane (54.43 g) and1,8-diazabicylo[5.4.0]undec-7-en (55.72 g) in methylene chloride (100mL) at 0-5° C. After the addition is complete, the reaction mixture isallowed to warm to room temperature, and stirred for 1 h. The reactionmixture is diluted with ethyl acetate and then washed successively withdiluted aqueous hydrochloric acid and brine. The ethyl acetate phase isdried over anhydrous sodium sulfate, filtered and concentrated invacuum. The residue is purified by recrystallization from hexane/ethylacetate to give 47.13 g of the title compound of the formula

as pale yellow crystals.

Step 3: Preparation of5-hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methylester

5-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester(46.0 g) is dissolved in concentrated sulfuric acid (200 mL, 97%) at0-5° C. To this cooled solution is added drop wise fuming nitric acid (7mL, 100%). After the addition is complete, the reaction mixture isallowed to warm to room temperature. TLC analysis (hexane/ethylacetate=4:1) after 30 min shows reaction completion. The reactionmixture is slowly poured onto an ice/water mixture (ca. 2 mL) and thecrystals were filtered off, washed thoroughly with water and dried invacuum to afford 47.0 g of the title compound of the formula

as pale yellow crystals.

Step 4: Preparation of6-nitro-5-trifluoromethanesulfonyloxy-2-trifluoromethyl-quinoline-7-carboxylicacid methyl ester

A solution of 5-hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylicacid methyl ester (6.82 g) in methylene chloride (50 mL) is treated withtriethylamne (6.69 g) and a catalytic amount of 4-dimethylamino pyridine(0.26 g). To this solution is added trifluoromethanesulfonic anhydride(9.1 g), maintaining the temperature at 25° C. for 1 h. The reactionmixture is diluted with methylene chloride and then washed successivelywith diluted aqueous hydrochloric acid, water, saturated aqueous sodiumbicarbonate and water. The methylene chloride phase is dried overanhydrous sodium sulfate, filtered and concentrated in vacuum. Theresidue is purified by column chromatography (hexane/ethyl acetate=9:1)to give 6.6 g of the title compound of the formula

as pale yellow crystals.

Step 5: Preparation of5-methyl-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methylester

A suspension of indium trichloride (2.0 g) in dry THF (5 mL) under anargon atmosphere is cooled to −78° C. and then treated drop wise withmethyl magnesium chloride (9.1 mL, 3 M in THF). The milky suspension isallowed to warm to room temperature and then added drop wise to arefluxing solution of bis(triphenylphosphine)palladium(II)chloride (0.19g) and6-nitro-5-trifluoromethanesulfonyloxy-2-trifluoromethyl-quinoline-7-carboxylicacid methyl ester (4.05 g) in dry THF (35 mL). The mixture is refluxedunder an argon atmosphere, monitoring by TLC. After reaction completion,the reaction mixture is concentrated in vacuum. The residue is taken upin diethyl ether and washed successively with diluted hydrochloric acidand brine. The diethyl ether phase is dried over anhydrous sodiumsulfate, filtered and concentrated in vacuum. The residue is purified bycolumn chromatography (hexane/ethyl acetate=4:1) to give 2.0 g of thetitle compound of the formula

as yellow crystals.

Step 6: Preparation of5-methyl-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid

5-Methyl-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methylester (3.78 g) is dissolved in 200 mL of methanol/water (3:1 mixture)and treated with lithium hydroxide hydrate (1.06 g) at room temperature.After reaction completion, the mixture is poured into ethyl acetate and2N hydrochloric acid, the organic phase is washed 3× with water, driedover sodium sulfate, filtered and concentrated in vacuum. The residue istriturated with a small amount of hexane. Filtration gives 3.50 g of thetitle compound of the formula

as white crystals.

Step 7: Preparation of6-amino-5-methyl-2-trifluoromethyl-quinoline-7-carboxylic acid

A solution of 5-methyl-6-nitro-2-trifluoromethyl-quinoline-7-carboxylicacid (1.40 g) in ethanol (100 mL) is hydrogenated at atmosphere pressureand ambient temperature in the presence of Raney-nickel catalyst. TLCanalysis after 12 h shows reaction completion. The mixture is filteredover hyflo and the filtrate concentrated in vacuum. The residue isrecrystallized from hexane/ethyl acetate to give 0.90 g of the titlecompound of the formula

as yellow crystals.

Step 8: Preparation of2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-9-methyl-6-trifluoromethyl-3-oxa-1,5-diaza-anthracen-4-one

A solution of 6-amino-5-methyl-2-trifluoromethyl-quinoline-7-carboxylicacid (0.60 g),2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylicacid (0.65 g, example 2, step 2) and pyridine (0.79 g) in acetonitrile(30 mL) is cooled to 0-5° C. and treated drop wise with methane sulfonylchloride (0.89 g) dissolved in 2 mL acetonitrile. TLC analysis(hexane/ethyl acetate 4:1) after 2 h shows reaction completion. Thereaction mixture is concentrated to ⅔ of the original volume in vacuumand poured onto 75 mL of ice/water. The resultant crystals are filteredoff, washed with water and dried in vacuum to give 1.0 g of the titlecompound of the formula

as orange crystals.

Step 9: Preparation ofN′-(6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2-trifluoromethyl-quinoline-7-carbonyl)-hydrazinecarboxylicacid methyl ester (20)

2-[2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-9-methyl-6-trifluoromethyl-3-oxa-1,5-diaza-anthracen-4-one(600 mg, can be prepared as in WO 2007/020050) is suspended in DMF andcarbazaic acid methyl ester (1.18 g) is added. The solution is stirredfor 15 h at 50° C. before it is quenched with water. The mixture is 2×extracted with ethyl acetate, the combined organic layer is 3× washedwith water, washed with brine, dried over magnesium sulfate andconcentrated in vacuum. The residue is purified by column chromatographyto afford the title compound of the formula

Then, Formulation Examples will be shown. All parts are by weight.

Formulation Example 1

Into a mixture of 35 parts of xylene and 35 parts ofN,N-dimethylformamide, 10 parts of any one of the present compounds (1)to (19) is dissolved, and then 14 parts of polyoxyethylene styrylphenylether and 6 parts of calcium dodecylbenzenesulfonate are added. Themixture is stirred thoroughly to obtain a 10% emulsion.

Formulation Example 2

To a mixture of 4 parts of sodium laurylsulfate, 2 parts of calciumligninsulfonate, 20 parts of synthetic hydrous silicon oxide fine powderand 54 parts of diatomaceous earth, 20 parts of any one of the presentcompounds (1) to (19) is added. The mixture is stirred thoroughly toobtain a 20% wettable agent.

Formulation Example 3

To 2 parts of any one of the present compounds (1) to (19), 1 part ofsynthetic hydrous silicon oxide fine powder, 2 parts of calciumligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay areadded, and then stirred thoroughly. Then, an appropriate amount of wateris added to the mixture. The mixture is further stirred, granulated witha granulator, and forced-air dried to obtain a 2% granule.

Formulation Example 4

Into an appropriate amount of acetone, 1 part of any one of the presentcompounds (1) to (19) is dissolved, and then 5 parts of synthetichydrous silicon oxide fine powder, 0.3 part of PAP and 93.7 parts offubasami clay are added. The mixture is stirred thoroughly. Then,acetone is removed from the mixture by evaporation to obtain a 1%powder.

Formulation Example 5

A mixture of 10 parts of any one of the present compounds (1) to (19);35 parts of white carbon containing parts of polyoxyethylene alkyl ethersulfate ammonium salt; and 55 parts of water is finely ground by a wetgrinding method to obtain a 10% flowable agent.

Formulation Example 6

In 5 parts of xylene and 5 parts of trichloroethane, 0.1 part of any oneof the present compounds (1) to (19) is dissolved. The solution is mixedwith 89.9 parts of deodorized kerosene to obtain a 0.1% oil.

Formulation Example 7

In 0.5 ml of acetone, 10 mg of any one of the present compounds (1) to(19) is dissolved. The solution is mixed uniformly with 5 g of a solidfeed powder for an animal (solid feed powder for rearing and breedingCE-2, manufactured by CLEA Japan, Inc.), and then dried by evaporationof acetone to obtain poison bait.

Then, it will be shown by Test Examples that the present compound iseffective in controlling harmful arthropods. In the Test Example,controlling values were calculated by the following equation:Controlling value(%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein

Cb: the number of worms in a non-treated section before treatment

Cai: the number of worms in a non-treated section on observation

Tb: the number of worms in a treated-section before treatment

Tai: the number of worms in a treated-section on observation.

Test Example 1

Preparations of the test compounds obtained in Formulation Example 5were diluted with water so that the active ingredient concentrationbecame 500 ppm, to prepare test spray solutions.

At the same time, cabbage was planted in a polyethylene cup, and grownuntil the third true leaf or the fourth true leaf was developed. Thetest spray solution as described above was sprayed in an amount of 20ml/cup on the cabbage.

After the spray solution on the cabbage was dried, 10 third-instarlarvae of diamondback moths (Plutella xylostella) were put on thecabbage. After 5 days, the number of diamondback moths was counted, andthe controlling value was calculated by the above equation.

As a result, the test spray solutions of the present compounds (1), (2),(3), (4), (5), (7), (8), (9), (10), (11), (14), (15), (16), (17) and(19) each exhibited a controlling value of 90% or more.

Furthermore, preparations of the test compound (7) and a comparativecompound of the formula

obtained in a formulation according to Formulation Example 5 werediluted with water so that the active ingredient concentration became0.2 ppm, to prepare test spray solution.

At the same time, cabbage was planted in a polyethylene cup, and grownuntil the third true leaf or the fourth true leaf was developed. Thetest spray solution as described above was sprayed in an amount of 20ml/cup on the cabbage.

After the spray solution on the cabbage was dried, 10 third-instarlarvae of diamondback moths (Plutella xylostella) were put on thecabbage. After 5 days, the number of diamondback moths was counted, andthe controlling value was calculated by the above equation.

Compound (7) exhibited a control value of more than 80%, whereas thecomparison compound of the above formula exhibited less than 80%control.

Test Example 2

Preparations of the test compounds obtained in Formulation Example 5were diluted with water so that the active ingredient concentrationbecame 500 ppm to prepare test spray solutions.

At the same time, cucumber was planted in a polyethylene cup, and wasgrown until the first true leaf was developed. About 30 cotton aphidswere put on the cucumber. One day after, the test spray solution asdescribed above was sprayed in an amount of 20 ml/cup on the cucumber.Six days after spraying, the number of cotton aphids (Aphis gossypii)was counted, and a controlling value was calculated by the aboveequation.

As a result, the test spray solutions of the present compounds (1), (2),(3), (4), (5), (7), (8), (9), (10), (11), (14), (15), (16), (18) and(19) each exhibited a controlling value of 90% or more.

Test Example 3

Preparations of the test compounds obtained in Formulation Example 5were diluted with water so that the active ingredient concentrationbecame 500 ppm to prepare test spray solutions.

At the same time, cabbage was planted in a polyethylene cup, and grownuntil the third true leaf or the fourth true leaf was developed. Thetest spray solution as described above was sprayed in an amount of 20ml/cup on the cabbage. After the spray solution sprayed on the cabbagewas dried, 10 fourth-instar larvae of Spodoptera litura were put on thecabbage. After 5 days, the number of Spodoptera litura surviving on thecabbage leaves was counted, and a controlling value was calculated bythe above equation.

As a result, the test spray solutions of the present compounds (1), (3),(4), (5), (7), (8), (9), (10), (11), (14), (15), (16) and (17) eachexhibited a controlling value of 80% or more.

Test Example 4

Preparations of the test compounds obtained in Formulation Example 5were diluted with water so that the active ingredient concentrationbecame 500 ppm to prepare test spray solutions.

At the same time, 20 ml of the test spray solution as described abovewas sprayed to an apple seedling (28 day-old seeding, tree height: about15 cm) planted in a plastic cup. The apple seedling was air-dried tosuch an extent that the spray solution sprayed on the apple seedling wasdried. About 30 first-instar larvae of Adoxophyes orana fasciata werereleased. Seven days after spraying, the number of worms surviving onthe apple seedling was counted, and a controlling value was calculatedby the above equation.

As a result, the test spray solutions of the present compounds (1), (2),(3), (4), (5), (7), (8), (14), (15) and (19) each exhibited acontrolling value of 90% or more.

Test Example 5

Preparations of the test compounds obtained in Formulation Example 5were diluted with water so that the active ingredient concentrationbecame 500 ppm to prepare test spray solutions.

At the same time, cucumber was planted in a polyethylene cup, and wasgrown until the first true leaf was developed. The test spray solutionas described above was sprayed in an amount of 20 ml/cup on thecucumber. After the spray solution on the cucumber was dried, the firsttrue leaf was cut and then placed on a filter paper (diameter: 70 mm)containing water in a polyethylene cup (diameter: 110 mm). On thecucumber leaf, 20 larvae of Franklinella occidentalis were released, andthe polyethylene cup was capped. Seven days after spraying, thepercentage of leaf area damaged by the insect was examined.

As a result, the test spray solutions of the present compounds (1), (2),(3), (4), (7), (8), (9), (10), (11), (14), (15) and (16) each suppressedthe feeding damage to the level of damaged area of 5% or less.

Test Example 6

Preparations of the test compounds obtained in Formulation Example 5were diluted with water so that the active ingredient concentrationbecame 500 ppm to prepare test spray solutions.

At the same time, cabbage was planted in a polyethylene cup, and grownuntil the first true leaf was developed. All leaves excluding the firsttrue leaf were cut off. On the first true leaf, adults of silver leafwhitefly, Bemisia argentifolii (or biotype B of tobacco whitefly,Bemisia tabaci) were released and allowed to lay eggs for about 24hours. The cabbage was retained in a greenhouse for 8 days. When larvaehatched from the laid eggs, the test spray solution as described abovewas sprayed in an amount of 20 ml/cup to the cabbage. Seven days afterspraying, the number of larvae surviving on the cabbage was counted, anda controlling value was calculated by the above equation.

As a result, the test spray solutions of the present compounds (7), (8),(9), (10), (11), (14) and (15) each exhibited a controlling value of 90%or more.

INDUSTRIAL APPLICABILITY

According to the present invention, since the hydrazide compound of thepresent invention has excellent efficacy of controlling pests, it isuseful as an active ingredient of a pesticide.

1. A hydrazide compound represented by the formula (1), an N-oxidethereof or suitable salt thereof:

wherein A¹ and A² independently represent an oxygen atom or a sulfuratom; E represents, together with the two contiguous linking carbonatoms, a 5- or 6-membered heteroaromatic ring system or an 8-, 9- or10-membered fused heterobicyclic ring system; R¹ represents a hydrogenatom, C1-C6 alkyl optionally substituted with one or more halogen atoms,C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms, C2-C6 alkenyl optionallysubstituted with one or more halogen atoms, C2-C6 alkynyl optionallysubstituted with one or more halogen atoms, C3-C6 cycloalkyl optionallysubstituted with one or more halogen atoms, C1-C6 alkylthio optionallysubstituted with one or more halogen atoms, C1-C6 alkylsulfinyloptionally substituted with one or more halogen atoms, C1-C6alkylsulfonyl optionally substituted with one or more halogen atoms,C2-C6 alkylcarbonyl optionally substituted with one or more halogenatoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6trialkylsilyl; or represents phenyl, C7-C9 phenylalkyl orphenylcarbonyl: each said phenyl ring optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6)C1-C6 alkyl optionally substituted with one or more halogen atoms, (7)C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyloptionally substituted with one or more halogen atoms, (11) C2-C6alkenyl optionally substituted with one or more halogen atoms, (12)C2-C6 alkynyl optionally substituted with one or more halogen atoms,(13) C3-C6 cycloalkyl optionally substituted with one or more halogenatoms, (14) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21)C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl; R² and R³ independently represent a hydrogen atom, C1-C6alkyl optionally substituted with one or more halogen atoms, C2-C6cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionally substitutedwith one or more halogen atoms, C2-C6 alkenyl optionally substitutedwith one or more halogen atoms, C2-C6 alkynyl optionally substitutedwith one or more halogen atoms, C3-C6 cycloalkyl optionally substitutedwith one or more halogen atoms, C1-C6 alkylthio optionally substitutedwith one or more halogen atoms, C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6trialkylsilyl; or represents phenyl, C7-C9 phenylalkyl orphenylcarbonyl: each said phenyl ring optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6)C1-C6 alkyl optionally substituted with one or more halogen atoms, (7)C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyloptionally substituted with one or more halogen atoms, (11) C2-C6alkenyl optionally substituted with one or more halogen atoms, (12)C2-C6 alkynyl optionally substituted with one or more halogen atoms,(13) C3-C6 cycloalkyl optionally substituted with one or more halogenatoms, (14) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21)C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl; or R² and R³ are taken together with the two nitrogenatoms to which they are attached to form a 5- to 8-membered ringcontaining two nitrogen atoms, one or more CH₂ or C(═O), and optionallyone or two ring members selected from the group consisting of (1) anoxygen atom, (2) a sulfur atom, (3) S(═O), (4) S(═O)₂ and (4) NR^(a)(wherein R^(a) represents C1-C6 alkyl optionally substituted with one ormore halogen atoms, C2-C6 alkoxycarbonyl optionally substituted with oneor more halogen atoms, or a phenyl optionally substituted with one ormore independent substituents from the group consisting of (1) a halogenatom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted withone or more halogen atoms, (5) C1-C6 alkoxy optionally substituted withone or more halogen atoms, (6) C1-C6 alkylthio optionally substitutedwith one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, (9) C1-C6alkylamino optionally substituted with one or more halogen atoms, (10)C2-C6 dialkylamino optionally substituted with one or more halogenatoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with oneor more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionallysubstituted with one or more halogen atoms and (14) C3-C6dialkylaminocarbonyl optionally substituted with one or more halogenatoms); and wherein the ring at the carbon atoms is optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, and (3) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms; R⁴ represents ahalogen atom, cyano, nitro, hydroxyl, carboxyl, C1-C6 alkyl optionallysubstituted with one or more halogen atoms, C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, C2-C6 cyanoalkyl, C2-C6alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6alkenyl optionally substituted with one or more halogen atoms, C2-C6alkynyl optionally substituted with one or more halogen atoms, C3-C6cycloalkyl optionally substituted with one or more halogen atoms, C1-C6alkylthio optionally substituted with one or more halogen atoms, C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms,C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino,C2-C6 alkylcarbonyl optionally substituted with one or more halogenatoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or represents a phenyl,benzyl, phenoxy, or a 5- or 6-membered heteroaromatic ring, each ringoptionally substituted with one or more substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4)hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with oneor more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxyoptionally substituted with one or more halogen atoms, (9) C2-C6cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one ormore halogen atoms, (11) C2-C6 alkenyl optionally substituted with oneor more halogen atoms, (12) C2-C6 alkynyl optionally substituted withone or more halogen atoms, (13) C3-C6 cycloalkyl optionally substitutedwith one or more halogen atoms, (14) C1-C6 alkylthio optionallysubstituted with one or more halogen atoms. (15) C1-C6 alkylsulfinyloptionally substituted with one or more halogen atoms, (16) C1-C6alkylsulfonyl optionally substituted with one or more halogen atoms,(17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl,(22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24)C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl; n representsan integer of 0 to 3 (provided that, when n is an integer of 2 or more,R^(4′)s may be the same or different); Q represents Q1, Q2, Q3, Q4, Q5or Q6: Q¹: —C(=A³¹)—R⁶ Q²: —C(=A³²)—OR⁷ Q³: —C(=A³³)—SR⁸ Q⁴:—C(=A³⁴)—NR⁹R¹⁰ Q⁵: —S(O)_(m)—R¹¹ Q6: —S(O)_(m)—NR¹²R¹³, A³¹, A³², A³³and A³⁴ represent an oxygen atom, or a sulfur atom; m represents aninteger of 0 to 2; R⁶ represents a hydrogen atom; C2-C6 alkenyloptionally substituted with one or more halogen atoms; C2-C6 alkynyloptionally substituted with one or more halogen atoms; C1-C6 alkyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) C1-C6alkoxy optionally substituted with one or more halogen atoms, (3) C1-C6alkylthio optionally substituted with one or more halogen atoms, (4)C1-C6 alkylsulfinyl optionally substituted, with one or more halogenatoms, (5) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (6) C2-C6 dialkylamino optionally substituted with one ormore halogen atoms, and (7) C3-C6 cycloalkyl optionally substituted withone or more halogen atoms; C3-C6 cycloalkyl optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted withone or more halogen atoms; phenyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarhonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; naphthyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 5- to 6-memberedheteroaryl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms; 3- to 8-membered non-aromatic heterocyclic ringoptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, and (2) C1-C6alkyl optionally substituted with one or more halogen atoms; C7-C9phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ring optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms; R⁷and R⁸ represent C1-C6 alkyl optionally substituted with one or morehalogen atoms; C2-C6 alkoxyalkyl optionally substituted with one or morehalogen atoms; C2-C6 alkenyl optionally substituted with one or morehalogen atoms; C2-C6 alkynyl optionally substituted with one or morehalogen atoms; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms and (5) C1-C6alkoxy optionally substituted with one or more halogen atoms; or C7-C9phenylalkyl whose phenyl ring moiety optionally is substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; R⁹ and R¹⁰independently represent a hydrogen atom; C1-C6 alkyl optionallysubstituted with one or more halogen atoms; C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms; C2-C6 alkenyl optionallysubstituted with one or more halogen atoms; C2-C6 alkynyl optionallysubstituted with one or more halogen atoms; C3-C6 cycloalkyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms; phenyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, (5) C1-C6alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms and (5) C1-C6alkoxy optionally substituted with one or more halogen atoms; or C7-C9phenylalkyl whose phenyl ring moiety optionally is substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; R¹¹ representsC1-C6 alkyl optionally substituted with one or more halogen atoms; C3-C6cycloalkyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,and (2) C1-C6 alkyl optionally substituted with one or more halogenatoms; or a phenyl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms; 5- to 6-membered heteroaryl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms; or3- to 8-membered non-aromatic heterocyclic ring optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms; R¹² and R¹³ independentlyrepresent C1-C6 alkyl optionally substituted with one or more halogenatoms; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; or phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; J represents J1or J2:

 wherein X^(a), Y^(a), Z^(a), X^(b), Y^(b) and Z^(b) independentlyrepresent CH or a nitrogen atom; R^(19a) and R^(19b) represent ahydrogen atom; C1-C6 alkyl optionally substituted with one or morehalogen atoms; C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionallysubstituted with one or more halogen atoms; C2-C6 alkenyl optionallysubstituted with one or more halogen atoms; C2-C6 alkynyl optionallysubstituted with one or more halogen atoms; C3-C6 cycloalkyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms; phenyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, (5) C1-C6alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms, (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms. (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; C7-C9 phenylalkyl whose phenyl ring is optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, (5) C1-C6alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; or C7-C9 pyridinylalkyl whose pyridine ring isoptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; R^(20a) and R^(20b)represent a halogen atom; cyano; nitro; thiocyanato; C1-C6 alkyloptionally substituted with one or more halogen atoms; C1-C6 alkoxyoptionally substituted with one or more halogen atoms; C2-C6cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substituted with one ormore halogen atoms; C2-C6 alkenyloxy optionally substituted with one ormore halogen atoms; C2-C6 alkynyloxy optionally substituted with one ormore halogen atoms; C1-C6 alkylthio optionally substituted with one ormore halogen atoms; C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms; C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms; phenyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 5- to 6-memberedheteroaryl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms; or phenoxy optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; p represents aninteger of 0 to 3 (provided that, when p is an integer of 2 or 3, two ormore R^(20a)'s may be the same or different); and q represents aninteger of 0 to 3 (provided that, when q is an integer of 2 or 3, two ormore R^(20b)'s may be the same or different).
 2. The compound accordingto claim 1, wherein E is a 5- or 6-membered heteroaromatic ring.
 3. Thecompound according to claim 1 or 2, wherein A¹ and A² are oxygen atoms;and R¹ is a hydrogen atom or alkyl optionally substituted with one ormore halogen atoms.
 4. The compound according to claim 1, wherein J isJ-1.1, J-1.2, J-2.1, J-2.2 or J-2.3:

wherein R^(19a) and R^(19b) represent a hydrogen atom; C1-C6 alkyloptionally substituted with one or more halogen atoms; C3-C6 cycloalkyloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom and (2) C1-C6alkyl optionally substituted with one or more halogen atoms; phenyl,optionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; 5- to 6-membered heteroaryloptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms and (5) C1-C6 alkoxy optionally substituted with one or morehalogen atoms; R^(20a) and R^(20b) represent a halogen atom, cyano,C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6alkoxy optionally substituted with one or more halogen atoms, C2-C6cyanoalkyloxy, C2-C6 alkoxyalkyloxy optionally substituted with one ormore halogen atoms, C2-C6 alkenyloxy optionally substituted with one ormore halogen atoms, C1-C6 alkylthio optionally substituted with one ormore halogen atoms, C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms; or phenyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 5- to 6-memberedheteroaryl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms or phenoxy optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom; (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; p represents aninteger of 0 to 3; and q represents an integer of 0 to 3 (provided that,when p is an integer of 2 or 3, two or more R^(20a)'s may be the same ordifferent and, when q is an integer of 2 or 3, two or more R^(20b)'s maybe the same or different).
 5. The compound according to claim 1, anN-oxide thereof or suitable salt thereof, wherein Q is Q1; A³¹ isoxygen; and R⁶ represents a hydrogen atom; C1-C6 alkyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (3) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (4) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (5)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (6) C2-C6 dialkylamino optionally substituted with one or morehalogen atoms, and (7) C3-C6 cycloalkyl optionally substituted with oneor more halogen atoms; C3-C6 cycloalkyl optionally substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with oneor more halogen atoms; phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom; (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms and (5) C1-C6alkoxy optionally substituted with one or more halogen atoms; 3- to8-membered non-aromatic heterocyclic optionally substituted with one ormore independent substituents selected from the grOup consisting of (1)a halogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms or C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each saidphenyl ring optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms.
 6. The compound according to claim 5, wherein A¹and A² are oxygen atoms.
 7. The compound according to claim 1, anN-oxide thereof or suitable salt thereof, wherein Q is Q2; A³² isoxygen; and R⁷ is C1-C6 alkyl optionally substituted with one or morehalogen atoms; C2-C6 alkenyl optionally substituted with one or morehalogen atoms; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms and (5) C1-C6alkoxy optionally substituted with one or more halogen atoms or C7-C9phenylalkyl whose ring moiety is optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms.
 8. The compoundaccording to claim 7, wherein A¹ and A² are oxygen atoms.
 9. Thecompound according to claim 1, an N-oxide thereof or suitable saltthereof, wherein Q is Q⁴; A³⁴ is oxygen; and R⁹ and R¹⁰ independentlyrepresent a hydrogen atom; C1-C6 alkyl optionally substituted with oneor more halogen atoms; C3-C6 cycloalkyl optionally substituted with oneor more independent substituents selected from the group consisting of(1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with oneor more halogen atoms; phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms and (5) C1-C6alkoxy optionally substituted with one or more halogen atoms or C7-C9phenylalkyl whose ring moiety is optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms.
 10. The compoundaccording to claim 9, wherein A¹ and A² are oxygen atoms.
 11. Ahydrazide compound represented by the formula (II-1) or (II-2);

wherein X^(a) represents a nitrogen atom or CR^(20ax); Y and Z representindependently a nitrogen atom or CR^(4b), but not Y and Z are CR^(4b) atthe same time; R¹ represents a hydrogen atom or C 1-C6 alkyl optionallysubstituted with one or more halogen atoms; R² and R³ independentlyrepresent a hydrogen atom, C1-C6 alkyl optionally substituted with oneor more halogen atoms, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6alkenyl optionally substituted with one or more halogen atoms, C2-C6alkynyl optionally substituted with one or more halogen atoms, C3-C6cycloalkyl optionally substituted with one or more halogen atoms, C1-C6alkylthio optionally substituted with one or more halogen atoms, C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms,C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6trialkylsilyl; or represents phenyl, C7-C9 phenylalkyl orphenylcarbonyl: each said phenyl ring optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6)C1-C6 alkyl optionally substituted with one or more halogen atoms, (7)C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one ormore halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyloptionally substituted with one or more halogen atoms, (11) C2-C6alkenyl optionally substituted with one or more halogen atoms, (12)C2-C6 alkynyl optionally substituted with one or more halogen atoms,(13) C3-C6 cycloalkyl optionally substituted with one or more halogenatoms, (14) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21)C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6trialkylsilyl; or R² and R³ are taken together with the two nitrogenatoms to which they are attached to form a 5- to 8-membered ringcontaining two nitrogen atoms, one or more CH₂ or C(═O), and optionallyone or two ring members selected from the group consisting of (1) anoxygen atom, (2) a sulfur atom, (3) S(═O), (4) S(═O)₂ and (4) NR^(a)(wherein R^(a) represents C1-C6 alkyl optionally substituted with one ormore halogen atoms, C2-C6 alkoxycarbonyl optionally substituted with oneor more halogen atoms, or a phenyl optionally substituted with one ormore independent substituents from the group consisting of (1) a halogenatom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted withone or more halogen atoms, (5) C1-C6 alkoxy optionally substituted withone or more halogen atoms, (6) C1-C6 alkylthio optionally substitutedwith one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, (9) C1-C6alkylamino optionally substituted with one or more halogen atoms, (10)C2-C6 dialkylamino optionally substituted with one or more halogenatoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or morehalogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with oneor more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionallysubstituted with one or more halogen atoms and (14) C3-C6dialkylaminocarbonyl optionally substituted with one or more halogenatoms); and wherein the ring at the carbon atoms is optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, and (3) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms; R^(4a), R^(4b)and R^(4c) independently represent a halogen atom, cyano, nitro,hydroxyl, carboxyl, C1-C6 alkyl optionally substituted with one or morehalogen atoms, C2-C6 alkoxy optionally substituted with one or morehalogen atoms, C2-C6 cyanoalkyl C2-C6 alkoxyalkyl optionally substitutedwith one or more halogen atoms, C2-C6 alkenyl optionally substitutedwith one or more halogen atoms, C2-C6 alkynyl optionally substitutedwith one or more halogen atoms, C3-C6 cycloalkyl optionally substitutedwith one or more halogen atoms, C1-C6 alkylthio optionally substitutedwith one or more halogen atoms, C1-C6 alkylsulfinyl optionallysubstituted with one or more halogen atoms, C1-C6 alkylsulfonyloptionally substituted with one or more halogen atoms, C1-C6 alkylamino,C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyloptionally substituted with one or more halogen atoms, C2-C6alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl,C3-C6 trialkylsilyl; or represents independently phenyl, benzyl,phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionallysubstituted with one or more substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl,(5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or morehalogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl, (10)C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms,(11) C2-C6 alkenyl optionally substituted with one or more halogenatoms, (12) C2-C6 alkynyl optionally substituted with one or morehalogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one ormore halogen atoms, (14) C1-C6 alkylthio optionally substituted with oneor more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substitutedwith one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionallysubstituted with one or more halogen atoms, (17) C 1-C6 alkylamino, (18)C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl,(23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and(25) C3-C6 trialkylsilyl; M is a hydrogen atom; C1-C6 alkyl optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (3) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (4) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (5)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (6) C2-C6 dialkylamino optionally substituted with one or morehalogen atoms, and (7) C3-C6 cycloalkyl optionally substituted with oneor more halogen atoms; C1-C6 alkoxy optionally substituted with one ormore halogen atoms; C1-C6 alkylthio optionally substituted with one ormore halogen atoms; C1-C6 alkylamino; C2-C8 dialkylamino; phenyl, C7-C9phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ring optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, and (5)C1-C6 alkoxy optionally substituted with one or more halogen atoms; 5-to 6-membered heteroaryl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; or 3- to8-membered non-aromatic heterocyclic ring optionally substituted withone or more independent substituents selected from the group consistingof (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted withone or more halogen atoms; R^(19ax) represents a hydrogen atom; C1-C6alkyl optionally substituted with one or more halogen atoms; C2-C6cyanoalkyl; C2-C6 alkoxyalkyl optionally substituted with one or morehalogen atoms; C2-C6 alkenyl optionally substituted with one or morehalogen atoms; C2-C6 alkenyl optionally substituted with one or morehalogen atoms; C3-C6 cycloalkyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, and (2) C1-C6 alkyl optionally substituted with one ormore halogen atoms; phenyl optionally substituted with one or moreindependent substituents selected from the group consisting of (1) ahalogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms, (5) C1-C6 alkoxy optionallysubstituted with one or more halogen atoms, (6) C1-C6 alkylthiooptionally substituted with one or more halogen atoms, (7) C1-C6alkylsulfinyl optionally substituted with one or more halogen atoms, (8)C1-C6 alkylsulfonyl optionally substituted with one or more halogenatoms, (9) C1-C6 alkylamino optionally substituted with one or morehalogen atoms, (10) C2-C6 dialkylamino optionally substituted with oneor more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substitutedwith one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionallysubstituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; 5- to 6-membered heteroaryl optionally substitutedwith one or more independent substituents selected from the groupconsisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyloptionally substituted with one or more halogen atoms, (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; C7-C9 phenylalkyl whose phenyl ring is optionallysubstituted with one or more independent substituents selected from thegroup consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6alkyl optionally substituted with one or more halogen atoms, (5) C1-C6alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6alkylthio optionally substituted with one or more halogen atoms, (7)C1-C6 alkylsulfinyl optionally substituted with one or more halogenatoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or morehalogen atoms, (9) C1-C6 alkylamino optionally substituted with one ormore halogen atoms, (10) C2-C6 dialkylamino optionally substituted withone or more halogen atoms, (11) C2-C6 alkylcarbonyl optionallysubstituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyloptionally substituted with one or more halogen atoms, (13) C2-C6alkylaminocarbonyl optionally substituted with one or more halogen atomsand (14) C3-C6 dialkylaminocarbonyl optionally substituted with one ormore halogen atoms; or C7-C9 pyridinylalkyl whose pyridine ring isoptionally substituted with one or more independent substituentsselected from the group consisting of (1) a halogen atom, (2) cyano, (3)nitro, (4) C1-C6 alkyl optionally substituted with one or more halogenatoms, (5) C1-C6 alkoxy optionally substituted with one or more halogenatoms, (6) C1-C6 alkylthio optionally substituted with one or morehalogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substitutedwith one or more halogen atoms, (9) C1-C6 alkylamino optionallysubstituted with one or more halogen atoms, (10) C2-C6 dialkylaminooptionally substituted with one or more halogen atoms, (11) C2-C6alkylcarbonyl optionally substituted with one or more halogen atoms,(12) C2-C6 alkoxycarbonyl optionally substituted with one or morehalogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted withone or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionallysubstituted with one or more halogen atoms; R^(20ax), R^(20ay) andR^(20az) represent a halogen atom; cyano; nitro; thiocyanato; C1-C6alkyl optionally substituted with one or more halogen atoms; C1-C6alkoxy optionally substituted with one or more halogen atoms; C2-C6cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substituted with one ormore halogen atoms; C2-C6 alkenyloxy optionally substituted with one ormore halogen atoms; C2-C6 alkynyloxy optionally substituted with one ormore halogen atoms; C1-C6 alkylthio optionally substituted with one ormore halogen atoms; C1-C6 alkylsulfinyl optionally substituted with oneor more halogen atoms; C1-C6 alkylsulfonyl optionally substituted withone or more halogen atoms; phenyl optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms; 5- to 6-memberedheteroaryl optionally substituted with one or more independentsubstituents selected from the group consisting of (1) a halogen atom,(2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one ormore halogen atoms and (5) C1-C6 alkoxy optionally substituted with oneor more halogen atoms; or phenoxy optionally substituted with one ormore independent substituents selected from the group consisting of (1)a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionallysubstituted with one or more halogen atoms and (5) C1-C6 alkoxyoptionally substituted with one or more halogen atoms.
 12. The compoundaccording to claim 11, wherein R¹ is a hydrogen atom; R² is a hydrogenatom or C1-C6 alkyl optionally substituted with one or more halogenatoms; R³ is a hydrogen atom, C1-C6 alkyl optionally substituted withone or more halogen atoms or C2-C6 alkoxycarbonyl; R^(4a) is a halogenatom or C1-C6 alkyl optionally substituted with one or more halogenatoms; R^(4c) is a hydrogen atom, a halogen atom, cyano or C1-C6 alkyloptionally substituted with one or more halogen atoms; R^(19a) is

 wherein X^(b) is a nitrogen atom or CR^(21a); R^(20ax) and R^(20ay) areindependently a hydrogen atom, a halogen atom, C1-C6 alkyl optionallysubstituted with one or more halogen atoms, C1-C6 alkoxy optionallysubstituted with one or more halogen atoms or C1-C6 alkylthio optionallysubstituted with one or more halogen atoms; R^(20az) is a hydrogen atom;and R^(21a), R^(21b) and R^(21c) are independently selected from thegroup consisting of a hydrogen atom, a halogen atom or C1-C6 alkyloptionally substituted with one or more halogen atoms.
 13. The compoundaccording to claim 12, wherein X^(a) and X^(b) are nitrogen atoms; Y isCH: and Z is a nitrogen atom.
 14. The compound according to claim 12,wherein X^(a) and X^(b) are nitrogen atoms; Y is a nitrogen atom; and Zis CH.
 15. The compound according to claim 12, wherein R^(4b) is ahydrogen atom.
 16. The compound according to claim 15, wherein M is ahydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino orC2-C8 dialkylamino.
 17. The compound according to claim 16, wherein R²is a hydrogen atom, methyl or ethyl; R³ is a hydrogen atom, methyl,ethyl or methoxycarbonyl; R^(4a) is methyl, chloro, bromo or iodo;R^(4c) is hydrogen, fluoro, chloro, bromo, iodo or cyano; R^(20ay) iscchloro, bromo, iodo, trifluoromethyl or pentafluoroethoxy; R^(21b) is ahydrogen atom; R^(21c) is chloro or bromo; and M is hydrogen, methoxy,ethoxy, methylamino or dimethylamino.
 18. The compound of claim 17,wherein R² is a hydrogen atom; R³ is methyl or ethyl; and M is ahydrogen atom.
 19. The compound of claim 17, wherein R² and R³ areindependently hydrogen, methyl or ethyl; and M is methoxy or ethoxy. 20.A pesticide comprising the compound according to claim 1 as an activeingredient.
 21. A method of controlling a pest which comprises applyingthe compound according to claim 1 directly to a pest, or to a placewhere a pest inhabits.